1-(3-溴苯基)丙-1-醇

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a flame-dried flask containing a solution of 1-(3-bromophenyl)propanol of Preparation 38 (3.50 g) and triethylamine (4.54 mL) in dry methylene chloride (18 mL) at 0° C. under nitrogen is added methanesulfonyl chloride (1.39 mL) over 1 min. The resulting mixture is stirred at 0° C. for 2 hrs, diluted with water (8 mL), and the layers are separated. The aqueous phase is extracted with methylene chloride (25 mL) and the combined organic phase is washed with saline (5 mL), dried over sodium sulfate, and concentrated under reduced pressure to give an oily intermediate. A mixture containing the intermediate and lithium bromide (1.42g) in acetone (50 mL) under nitrogen is refluxed for 4 hrs, cooled to RT, concentrated to remove acetone, re-diluted with methylene chloride (40 mL) and water (20 mL), and the layers are separated. The aqueous phase is extracted with methylene chloride (40 mL) and the combined organic phase is washed with saline (15 mL), dried over sodium sulfate, and concentrated to give a crude oil which is then chromatographed on silica gel (70-230 mesh, 250 g), eluting with ethyl acetate/hexane (5/95). Pooling of fractions with an Rf =0.63 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent under reduced pressure gives the title compound. To a flame-dried flask containing the layers are separated The aqueous phase is extracted with methylene chloride (25 mL) the combined organic phase is washed with saline (5 mL) dried over sodium sulfate concentrated under reduced pressure to give an oily intermediate is refluxed for 4 hrs cooled to RT concentrated to remove acetone re-diluted with methylene chloride (40 mL) and water (20 mL) the layers are separated The aqueous phase is extracted with methylene chloride (40 mL) the combined organic phase is washed with saline (15 mL) dried over sodium sulfate concentrated to give a crude oil which is then chromatographed on silica gel (70-230 mesh, 250 g) eluting with ethyl acetate/hexane (5/95) Pooling of fractions with an Rf =0.63 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent under reduced pressure

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a flame-dried flask containing a solution of 1-(3-bromophenyl)propanol of Preparation 38 (3.50 g) and triethylamine (4.54 mL) in dry methylene chloride (18 mL) at 0° C. under nitrogen is added methanesulfonyl chloride (1.39 mL) over 1 min. The resulting mixture is stirred at 0° C. for 2 hrs, diluted with water (8 mL), and the layers are separated. The aqueous phase is extracted with methylene chloride (25 mL) and the combined organic phase is washed with saline (5 mL), dried over sodium sulfate, and concentrated under reduced pressure to give an oily intermediate. A mixture containing the intermediate and lithium bromide (1.42g) in acetone (50 mL) under nitrogen is refluxed for 4 hrs, cooled to RT, concentrated to remove acetone, re-diluted with methylene chloride (40 mL) and water (20 mL), and the layers are separated. The aqueous phase is extracted with methylene chloride (40 mL) and the combined organic phase is washed with saline (15 mL), dried over sodium sulfate, and concentrated to give a crude oil which is then chromatographed on silica gel (70-230 mesh, 250 g), eluting with ethyl acetate/hexane (5/95). Pooling of fractions with an Rf =0.63 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent under reduced pressure gives the title compound. To a flame-dried flask containing the layers are separated The aqueous phase is extracted with methylene chloride (25 mL) the combined organic phase is washed with saline (5 mL) dried over sodium sulfate concentrated under reduced pressure to give an oily intermediate is refluxed for 4 hrs cooled to RT concentrated to remove acetone re-diluted with methylene chloride (40 mL) and water (20 mL) the layers are separated The aqueous phase is extracted with methylene chloride (40 mL) the combined organic phase is washed with saline (15 mL) dried over sodium sulfate concentrated to give a crude oil which is then chromatographed on silica gel (70-230 mesh, 250 g) eluting with ethyl acetate/hexane (5/95) Pooling of fractions with an Rf =0.63 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent under reduced pressure