Diethyl Ether → [2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-methanol

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Reaction Steps

Dissolve 2-(2,5-dimethoxy-phenyl)-cyclopentanecarboxylic acid ethyl ester (4.5 g, 16 mmol) in tetrahydrofuran (80 ml), add a 1.0M solution of lithium aluminum hydride in tetrahydrofuran (49 ml, 49 mmol), and stir at room temperature for 1 hour. Pour slowly into a mixture of ether and aqueous Rochelle's Salt, stir over night, separate layers, wash organic with brine, dry and concentrate to give the title compound (3.6 g, 94%): 1H NMR (CDCl3) δ 6.82-6.70 (m, 3H), 3.82 (s, 3H), 3.77 (s,−3H), 3.66-3.60 (m, 1H), 3.30-3.23 (m, 1H), 3.07-3.01 (m, 1H), 2.53-2.43 (m, 1H), 2.14-2.11 (m, 1H), 2.03-1.98 (m, 1H), 1.94-1.89 (m, 2H), 1.81-1.71 (m, 2H), 1.43-1.38 (m, 1H).

Provenance & Evidence