3-(5-甲基呋喃-2-基)丙-1-醇

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

实验步骤: To a solution of ethyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of the desired product. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The organic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified

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

实验步骤: To a solution of methyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of 3-(5-methyl-2-furyl)propan-1-ol. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The organic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified

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

实验步骤: Under nitrogen with stirring 5-methyl-2- 3- 2, 6-dimethyl-4-(2-methyl-tetrazol-5-yl) phenoxy!-propyl!-2,5-dimethoxy-2,5-dihydrofuran (820 mg, 1.8 mmol), 0.8 mL of methanol, and 1.5 mL of 1% aqueous acetic acid solution were combined at room temperature, refluxed for 10 min, and then cooled to room temperature. To the above solution was added hydrazine hydrate (0.26 mL) over a 2 min period, and the mixture was allowed to reflux for 1 h, and cooled to room temperature. The mixture was diluted with water, the aqueous layer was extracted with methylene chloride, and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford 180 mg (29 %) of 3,methyl-6- 3- 2,6-dimethyl-4-(2-methyltetrazol-5-yl)-phenoxy!propyl !-pyridazine (Formula I; R1, R2 =3,5-dimethyl, R3 =6-methyl, R4 =hydrogen, R5 =2-methyltetrazol-5-yl), m.p. 114°-115° C. were combined at room temperature refluxed for 10 min to reflux for 1 h cooled to room temperature the aqueous layer was extracted with methylene chloride the organic layer was washed with brine dried over magnesium sulfate concentrated in vacuo to afford 180 mg (29 %) of 3,methyl-6- 3- 2,6-dimethyl-4-(2-methyltetrazol-5-yl)-phenoxy

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

实验步骤: To a solution of ethyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of the desired product. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The organic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified

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

实验步骤: To a solution of methyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of 3-(5-methyl-2-furyl) propan-1-ol. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The organic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified

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

实验步骤: To a solution of ethyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwlse under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The orgaic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of the desired product. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The orgaic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified

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

实验步骤: To a solution of methyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of 3-(5-methyl-2-furyl)propan-1-ol. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The organic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified

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

实验步骤: To a solution of ethyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of the desired product. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The organic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified

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

实验步骤: To a solution of methyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of 3-(5-methyl-2-furyl)propan-1-ol. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The organic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified

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

实验步骤: Under nitrogen with stirring 5-methyl-2- 3- 2, 6-dimethyl-4-(2-methyl-tetrazol-5-yl) phenoxy!-propyl!-2,5-dimethoxy-2,5-dihydrofuran (820 mg, 1.8 mmol), 0.8 mL of methanol, and 1.5 mL of 1% aqueous acetic acid solution were combined at room temperature, refluxed for 10 min, and then cooled to room temperature. To the above solution was added hydrazine hydrate (0.26 mL) over a 2 min period, and the mixture was allowed to reflux for 1 h, and cooled to room temperature. The mixture was diluted with water, the aqueous layer was extracted with methylene chloride, and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford 180 mg (29 %) of 3,methyl-6- 3- 2,6-dimethyl-4-(2-methyltetrazol-5-yl)-phenoxy!propyl !-pyridazine (Formula I; R1, R2 =3,5-dimethyl, R3 =6-methyl, R4 =hydrogen, R5 =2-methyltetrazol-5-yl), m.p. 114°-115° C. were combined at room temperature refluxed for 10 min to reflux for 1 h cooled to room temperature the aqueous layer was extracted with methylene chloride the organic layer was washed with brine dried over magnesium sulfate concentrated in vacuo to afford 180 mg (29 %) of 3,methyl-6- 3- 2,6-dimethyl-4-(2-methyltetrazol-5-yl)-phenoxy

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

实验步骤: To a solution of ethyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of the desired product. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The organic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified

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

实验步骤: To a solution of methyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of 3-(5-methyl-2-furyl) propan-1-ol. the mixture was stirred for 30 min The solid was removed by filtration the filtrate was diluted with 20 mL of water extracted with methylene chloride The organic layer was washed with water dried over magnesium sulfate concentrated in vacuo The residue was purified