1-(5-chloro-2-methoxyphenyl)ethanol

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

Procedure: 1-(5-Chloro-2-methoxyphenyl)ethanol (Preparation 4, 6.97 g, 37.3 mmol), was dissolved in trifluoroacetic acid (20 mL). Triethylsilane (29.8 mL, 187 mmol) was added and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in ethyl acetate and washed with water. The organic phase was separated and concentrated in vacuo to afford the title compound (9 g, 141%, contains residual triethylsilane). This material was taken on crude in subsequent steps. The reaction mixture was concentrated in vacuo The resulting residue was dissolved in ethyl acetate washed with water The organic phase was separated concentrated in vacuo

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

Procedure: To a solution of 1-(5-chloro-2-methoxyphenyl)ethanone (7.97 g, 43.1 mmol) in anhydrous tetrahydrofuran (40 mL) at 0° C. was added a 1M solution of lithium aluminium hydride In THF (14.2 mL, 14.2 mmol). After 3 hours, ethyl acetate (200 mL) was added and the mixture was washed with a 1M aqueous solution of hydrogen chloride (50 mL). The organic phase was concentrated in vacuo to afford the title compound (6.97 g, 86%) the mixture was washed with a 1M aqueous solution of hydrogen chloride (50 mL) The organic phase was concentrated in vacuo