Methanol → (Cyclohexylmethoxy)acetic Acid Ethyl Ester

Participants

Reaction Steps

To a solution of cyclohexylmethanol (1.23 mL, 10.0 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (11 mg) followed by ethyl diazoacetate (1.05 mL, 10.0 mmol). The reaction mixture is stirred at RT for 30 min. To the reaction mixture is added MeOH, and the reaction mixture is rotary evaporated, and the residue dissolved in Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at to give 2.02 g of the product 419. 1H NMR (CDCl3) δ 4.22 (q, 2 H), 4.05 (s, 2 H), 3.33 (d, 2 H), 1.8-1.5 (m, 7 H), 1.4-1.1 (m, 5 H), 1.1-0.9 (m, 2 H); MS: m/z 200 (M++1).

Provenance & Evidence