1-(2-methoxyphenyl)propan-1-ol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a time-dried flask containing a solution of o-anisaldehyde (2.00 g) in dry tetrahydrofuran (9.8 mL) at 0° C. under nitrogen is added a solution of ethylmagnesium bromide (3M in diethyl ether, 5.4 mL) in dry tetrahydrofuran (5.4 mL) over 25 min. The resulting mixture is stirred at 0° C. for 1 hr, quenched with saturated aqueous ammonium chloride (15 mL), and the layers are separated. The aqueous phase is extracted with diethyl ether (2×30 mL) and the combined organic phase is washed with saline (15 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an oil which is then chromatographed on silica gel (230-400 mesh, 250 g), eluting with a gradient of ethyl acetate/hexane (5/95-10/90). Pooling of fractions having an Rf =0.44 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent gives the title compound. quenched with saturated aqueous ammonium chloride (15 mL) the layers are separated The aqueous phase is extracted with diethyl ether (2×30 mL) the combined organic phase is washed with saline (15 mL) dried over anhydrous magnesium sulfate concentrated under reduced pressure to give an oil which is then chromatographed on silica gel (230-400 mesh, 250 g) eluting with a gradient of ethyl acetate/hexane (5/95-10/90) by TLC (ethyl acetate/hexane, 25/75) and removal of solvent

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a time-dried flask containing a solution of o-anisaldehyde (2.00 g) in dry tetrahydrofuran (9.8 mL) at 0° C. under nitrogen is added a solution of ethylmagnesium bromide (3M in diethyl ether, 5.4 mL) in dry tetrahydrofuran (5.4 mL) over 25 min. The resulting mixture is stirred at 0° C. for 1 hr, quenched with saturated aqueous ammonium chloride (15 mL), and the layers are separated. The aqueous phase is extracted with diethyl ether (2×30 mL) and the combined organic phase is washed with saline (15 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an oil which is then chromatographed on silica gel (230-400 mesh, 250 g), eluting with a gradient of ethyl acetate/hexane (5/95-10/90). Pooling of fractions having an Rf =0.44 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent gives the title compound. quenched with saturated aqueous ammonium chloride (15 mL) the layers are separated The aqueous phase is extracted with diethyl ether (2×30 mL) the combined organic phase is washed with saline (15 mL) dried over anhydrous magnesium sulfate concentrated under reduced pressure to give an oil which is then chromatographed on silica gel (230-400 mesh, 250 g) eluting with a gradient of ethyl acetate/hexane (5/95-10/90) by TLC (ethyl acetate/hexane, 25/75) and removal of solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: o-Anisaldehyde (2.72 g) was dissolved in tetrahydrofuran (50 ml), and 0.93M magnesium ethylbromide—tetrahydrofuran solution (31.3 ml) was added dropwise under ice-cooling over 10 min. The mixture was stirred at room temperature for 2 hr. The reaction mixture was ice-cooled, and saturated aqueous ammonium chloride solution (40 ml) and water (40 ml) were added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (3.15 g). cooling over 10 min cooled the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried over magnesium sulfate concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)