Methanol → HCID 66960124, compound

Participants

Reaction Steps

To a stirred, rt, solution of 2-Et-3-O-MOM estrone 52 (743 mg, 2.18 mmol) in THF (10 mL)/methanol (40 mL) solution was added sodium borohydride (76 mg, 2 mmol). After one hour the reaction was quenched by addition of ammonium chloride (2 mL of saturated solution), diluted with ethyl acetate (50 mL) and water (25 mL), the organic layer separated and washed with water, brine, dried and evaporated. Column chromatography (hexane/ethyl acetate gradient) gave the desired alcohol 53 as a clear colourless oil (650 mg) which showed δH (400 MHz, CDCl3, ref. TMS=0) 7.09 (1H, s, ArH), 6.78 (1H, s, ArH), 5.17 (2H, s, OCH2), 3.69-3.78 (1H, m, CHOH) 3.48 (3H, s, OMe), 2.78-2.86 (2H, m, 6-CH2), 2.61 (2H, q, J 7.4, CH2Me), 1.24-2.38 (13H, m), 1.19 (3H, t, J 7.4, CH2Me) and 0.77 (3H, s, 18-CH3).

Provenance & Evidence