6-溴己基 乙酸甲酯

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

实验步骤: 20.1 g (0.16 mol) of DMAP were added to 297.4 g (1.64 mol) of 6-bromo-1-hexanol in 1500 ml of THF. A solution of 184.4 g (1.81 mol) of acetic anhydride in 300 ml of THF was added dropwise in such a way that the reaction temperature did not exceed 30° C. After completion of the addition, the mixture was stirred for a further 30 minutes. The reaction mixture was mixed with 500 ml of diisopropyl ether and extracted successively with 700 ml each of water, 2× saturated NaHCO3 solution and water. After drying over sodium sulfate, the solvent was removed in vacuo. 352.8 g (1.58 mol, 96%) of 6-bromohexyl acetate were obtained. did not exceed 30° C After completion of the addition extracted successively with 700 ml each of water, 2× saturated NaHCO3 solution and water After drying over sodium sulfate the solvent was removed in vacuo

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

实验步骤: In a 50-ml flask, zinc powder (98 mg, 1.5 mmol) was dried at 70° C. under high vacuum for 30 min. After back-filling with nitrogen, DMI (25 ml) was added followed by solid I2 (380 mg, 1.53 mmol) for Zn activation. The iodine color disappeared after stirring for 5 min. Neat 6-bromohexyl acetate (6.83 g, 30.61 mmol) was added and the mixture was stirred at 65-80° C. for 2-14 h, cooled to the room temperature, excess zinc was allowed to settle, and the organozinc solution 46 was transferred via cannula into a solution of anhydrous LiBr (5.32 g, 61, 23 mmol) in THF (50 ml). The solution of organozinc reagent in DMI-THF mixture was cooled to 0° C. and solution of PEPPSI-IPr (130 mg, 0.191 mmol) in DMI (3 ml) was added followed by a rapid addition of neat Br(CH2)11OTHP 47 (6.42 g, 19.13 mmol). The cooling bath was removed and the reaction mixture was stirred at room temperature for 9 h. Reaction mixture was quenched with aqueous NH4Cl solution (250 ml) and extracted with EtOAc (250 ml). The extract was washed with aqueous NH4Cl solution, dried over Na2SO4 and concentrated under reduced pressure. The crude product was chromatographed on silica gel in hexane-EtOAc (97:3) to give the compound 39 (7.09 g, 93%). the mixture was stirred at 65-80° C. for 2-14 h The cooling bath was removed the reaction mixture was stirred at room temperature for 9 h Reaction mixture was quenched with aqueous NH4Cl solution (250 ml) extracted with EtOAc (250 ml) The extract was washed with aqueous NH4Cl solution dried over Na2SO4 concentrated under reduced pressure The crude product was chromatographed on silica gel in hexane-EtOAc (97:3)

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

实验步骤: 20.1 g (0.16 mol) of DMAP were added to 297.4 g (1.64 mol) of 6-bromo-1-hexanol in 1500 ml of THF. A solution of 184.4 g (1.81 mol) of acetic anhydride in 300 ml of THF was added dropwise in such a way that the reaction temperature did not exceed 30° C. After completion of the addition, the mixture was stirred for a further 30 minutes. The reaction mixture was mixed with 500 ml of diisopropyl ether and extracted successively with 700 ml each of water, 2× saturated NaHCO3 solution and water. After drying over sodium sulfate, the solvent was removed in vacuo. 352.8 g (1.58 mol, 96%) of 6-bromohexyl acetate were obtained. did not exceed 30° C After completion of the addition extracted successively with 700 ml each of water, 2× saturated NaHCO3 solution and water After drying over sodium sulfate the solvent was removed in vacuo