5-(二甲氨基)-2-戊酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 20 gm (167 mMol) N,N-dimethyl-5-amino-2-pentanone, 14.5 gm (208 mMol) hydroxylamine hydrochloride, and 8.8 gm (83 mMol) sodium carbonate in 50 mL water was heated at reflux for 1.5 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane. The organic extracts were combined, dried over sodium sulfate and concentrated under reduced pressure. The residual oil crystallized on standing at room temperature. The solid was washed with hexane to provide 12.8 gm (54%) of the desired oxime as a colorless solid in two crops. was heated at reflux for 1.5 hours the reaction mixture was extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure The residual oil crystallized on standing at room temperature The solid was washed with hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 20 gm (167 mMol) N,N-dimethyl-5-amino-2-pentanone, 14.5 gm (208 mMol) hydroxylamine hydrochloride, and 8.8 gm (83 mMol) sodium carbonate in 50 mL water was heated at reflux for 1.5 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane. The organic extracts were combined, dried over sodium sulfate and concentrated under reduced pressure. The residual oil crystallized on standing at room temperature. The solid was washed with hexane to provide 12.8 gm (54%) of the desired oxime as a colorless solid in two crops. was heated at reflux for 1.5 hours the reaction mixture was extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure The residual oil crystallized on standing at room temperature The solid was washed with hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 21.77 gm (180.5 mMol) 5-chloro-2-pentanone, 13.40 gm (164.3 mMol) dimethylamine hydrochloride and 50.0 gm (361.8 mMol) potassium carbonate in 150 mL acetonitrile was stirred at room temperature for 2 days and then at reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The phases were separated and the aqueous phase again extracted with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The desired product was then isolated by distillation. at reflux for 2 hours The reaction mixture was then cooled to room temperature partitioned between water and dichloromethane The phases were separated the aqueous phase again extracted with dichloromethane dried over sodium sulfate concentrated under reduced pressure eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide concentrated under reduced pressure