Tetrahydrofuran → [2-(2-Methoxy-phenyl)-cyclohexyl]-methanol

Participants

Reaction Steps

Combine 2-(2-methoxy-phenyl)-cyclohexanecarboxylic acid ethyl ester (2.34 g, 8.9 mmol), lithium aluminum hydride (1.02 g, 26.7 mmol), and tetrahydrofuran (30.0 mL) at room temperature. Stir at rm temperature under nitrogen for 2 hours then add Rochelle's salt and ethyl acetate. Stir 18 hours then separate layers and wash with brine then dry over anhydrous sodium sulfate. Concentrate to yield the titled compound (1.86 g, 95%). TLC Rf=0.08 in 10% ethyl acetate/hexanes. 1H NMR (CDCl3): 7.2 (m, 2H), 6.9 (m, 2H), 3.8 (s, 3H), 3.5 (m, 1H), 3.4 (m, 1H), 3.3 (m, 1H), 2.3 (m, 1H), 1.8 (m, 2H), 1.5 (m, 6H).

Provenance & Evidence