(4-fluoro-2-methoxyphenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: An ice-cold solution of 5.6 g of 4-fluoro-2-methoxy-benzaldehyde in 75 ml of methanol was treated portionwise (5 portions within 50 minutes) with 1.51 g (40 mmol) of sodium borohydride and the reaction mixture was stirred for another 1 hour at room temperature. A dispersion of 7 g of potassium hydrogencarbonate in 20 ml of water was added and the mixture stirred for 30 minutes at room temperature. Thereupon, most of the methanol was evaporated under reduced pressure and the residue extracted with dichloromethane. The organic phase was separated, dried and concentrated under reduced pressure to yield 5.15 g (91% of theory) of (4-fluoro-2-methoxy-phenyl)-methanol as a white solid; MS: 156 (M)+. the mixture stirred for 30 minutes at room temperature Thereupon, most of the methanol was evaporated under reduced pressure the residue extracted with dichloromethane The organic phase was separated dried concentrated under reduced pressure

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

Procedure: An ice-cold solution of 5.6 g of 4-fluoro-2-methoxy-benzaldehyde in 75 ml of methanol was treated portionwise (5 portions within 50 minutes) with 1.51 g (40 mmol) of sodium borohydride and the reaction mixture was stirred for another 1 hour at room temperature. A dispersion of 7 g of potassium hydrogencarbonate in 20 ml of water was added and the mixture stirred for 30 minutes at room temperature. Thereupon, most of the methanol was evaporated under reduced pressure and the residue extracted with dichloromethane. The organic phase was separated, dried and concentrated under reduced pressure to yield 5.15 g (91% of theory) of (4-fluoro-2-methoxy-phenyl)-methanol as a white solid; MS: 156 (M)+. the mixture stirred for 30 minutes at room temperature Thereupon, most of the methanol was evaporated under reduced pressure the residue extracted with dichloromethane The organic phase was separated dried concentrated under reduced pressure

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

Procedure: Triethylamine (0.84 ml, 6.03 mmol) was added to a solution of 4-fluoro-2-methoxybenzylalcohol (310.8 mg, 1.99 mmol) in DMSO (7 ml). Pyridine sulfur trioxide (938.6 mg, 5.90 mmol) was added portionwise to the mixture checking raise of the temperature. The mixture was stirred for 1 hour. The mixture was added to 5% KHSO4 aqueous solution, extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=5/1) to give the title compound (293.3 mg; 96%). checking raise of the temperature extracted three times with ethyl acetate dried over MgSO4 The mixture was concentrated purified by silica gel chromatography (hexane/ether=5/1)

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

Procedure: Triethylamine (0.84 ml, 6.03 mmol) was added to a solution of 4-fluoro-2-methoxybenzylalcohol (310.8 mg, 1.99 mmol) in DMSO (7 ml). Pyridine sulfur trioxide (938.6 mg, 5.90 mmol) was added portionwise to the mixture checking raise of the temperature. The mixture was stirred for 1 hour. The mixture was added to 5% KHSO4 aqueous solution, extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=5/1) to give the title compound (293.3 mg; 96%). checking raise of the temperature extracted three times with ethyl acetate dried over MgSO4 The mixture was concentrated purified by silica gel chromatography (hexane/ether=5/1)

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

Procedure: To a suspension of LiAlH4 (94.6 mg, 2.49 mmol) in THF (3 ml) was added dropwise a solution of methyl 4-fluoro-2-methoxybenzoate obtained in Example 23-2) (273.3 mg, 1.48 mmol) in THF (3 ml). The mixture was stirred for 1 hour. To the mixture was added dropwise aqueous THF followed by water. The mixture was extracted three times with ethyl acetate and dried over MgSO4. The solvent was evaporated to give the crude title compound (310.8 mg; 83%). The mixture was extracted three times with ethyl acetate dried over MgSO4 The solvent was evaporated

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: An ice-cold solution of 5.6 g of 4-fluoro-2-methoxy-benzaldehyde in 75 ml of methanol was treated portionwise (5 portions within 50 minutes) with 1.51 g (40mmol) of sodium borohydride and the reaction mixture was stirred for another 1 hour at room temperature. A dispersion of 7 g of potassium hydrogencarbonate in 20 ml of water was added and the mixture stirred for 30 minutes at room temperature. Thereupon, most of the methanol was evaporated under reduced pressure and the residue extracted with dichloromethane. The organic phase was separated, dried and concentrated under reduced pressure to yield 5.15 g (91% of theory) of (4-fluoro-2-methoxy-phenyl)-methanol as a white solid; MS: 156 (M)+. the mixture stirred for 30 minutes at room temperature Thereupon, most of the methanol was evaporated under reduced pressure the residue extracted with dichloromethane The organic phase was separated dried concentrated under reduced pressure

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

Procedure: An ice-cold solution of 5.6 g of 4-fluoro-2-methoxy-benzaldehyde in 75 ml of methanol was treated portionwise (5 portions within 50 minutes) with 1.51 g (40 mmol) of sodium borohydride and the reaction mixture was stirred for another 1 hour at room temperature. A dispersion of 7 g of potassium hydrogencarbonate in 20 ml of water was added and the mixture stirred for 30 minutes at room temperature. Thereupon, most of the methanol was evaporated under reduced pressure and the residue extracted with dichloromethane. The organic phase was separated, dried and concentrated under reduced pressure to yield 5.15 g (91% of theory) of (4-fluoro-2-methoxy-phenyl)-methanol as a white solid; MS: 156 (M)+. the mixture stirred for 30 minutes at room temperature Thereupon, most of the methanol was evaporated under reduced pressure the residue extracted with dichloromethane The organic phase was separated dried concentrated under reduced pressure

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

Procedure: Triethylamine (0.84 ml, 6.03 mmol) was added to a solution of 4-fluoro-2-methoxybenzylalcohol (310.8 mg, 1.99 mmol) in DMSO (7 ml). Pyridine sulfur trioxide (938.6 mg, 5.90 mmol) was added portionwise to the mixture checking raise of the temperature. The mixture was stirred for 1 hour. The mixture was added to 5% KHSO4 aqueous solution, extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=5/1) to give the title compound (293.3 mg; 96%). checking raise of the temperature extracted three times with ethyl acetate dried over MgSO4 The mixture was concentrated purified by silica gel chromatography (hexane/ether=5/1)

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

Procedure: To a suspension of LiAlH4 (94.6 mg, 2.49 mmol) in THF (3 ml) was added dropwise a solution of methyl 4-fluoro-2-methoxybenzoate obtained in Example 23-2) (273.3 mg, 1.48 mmol) in THF (3 ml). The mixture was stirred for 1 hour. To the mixture was added dropwise aqueous THF followed by water. The mixture was extracted three times with ethyl acetate and dried over MgSO4. The solvent was evaporated to give the crude title compound (310.8 mg; 83%). The mixture was extracted three times with ethyl acetate dried over MgSO4 The solvent was evaporated

Conditions: temp:0.00; pressure:0.00; stir: