Sodium Methoxide → HCID 90411588, compound

Participants

Reaction Conditions

Reaction Steps

Sodium methoxide, 25% in MeOH (6 ml) was added to asolution of 41 (8.7 g, 15.9 mmol) in 300 ml of MeOH. The reaction was stirred at 50° C. for 3 hrs, then treated with 5.3 g of solid triethylammonium chloride and concentrated. The obtained residue was partitioned between water and ethyl acetate. The organicphase was washed with saturated NaCl and dried over Na2SO4. Concentration of the extract gave an oil. The oil was chromatographed on silica eluting with 20 to 30% ethyl acetate in hexane to afford a crude product, which was re-crystallized from hexane (˜30 ml) at −20° C. to yield 5.4 g (76%) of 42 as white crystals. 1H NMR (DMSO-d6): δ 11.18 (s, 1H), 7.49 (d, J=7.5 Hz, 1H), 5.51 (d, J=7.5 Hz, 1H), 3.99 (m, 1H), 3.75 (m, 1H), 3.55 (m, 3H), 2.03 (m, 1H), 1.12 (d, J=6 Hz, 3H), 0.84 (s, 18H), 0.02 (s, 6H), 0.00 (s, 6H).

Provenance & Evidence