Ethyl 1-(2,3-dimethoxybenzyl)cycloheptane Carboxylate → [1-(2,3-Dimethoxybenzyl)cycloheptyl]methanol

Participants

Reaction Steps

The crude ester (26 g, 82 mmol, from Step B above), was dissolved in 400 mL anhydrous THF to which was added solid LiAlH4 (4.6 g, 123 mmol) in small portions at room temperature. The reaction was stirred at room temperature until TLC indicated completion. The reaction was then quenched with 1M HCl and diluted with ether. The layers were separated, and the organic layer was washed with 1M HCl, water, and brine. The organic layer was dried over MgSO4, filtered and evaporated. The resulting oil was purified by silica gel chromatography to give 20 g of the title product as a colorless oil.

Provenance & Evidence