Water → HCID 70022905, compound

Participants

Reaction Steps

To the acetates 11 (2.2 g, 4.0 mmol) in a mixture of methanol (60 mL) and dichloromethane (10 mL) was added potassium carbonate (0.1 eq, 55 mg, 0.4 mmol). After stirring for 4 h an additional portion of potassium carbonate (1.0 eq, 0.55 g, 4.0 mmol) was added. The mixture was stirred 16 h and more potassium carbonate (1.0 eq, 0.55 g, 4.0 mmol) was added. After 24 h water (100 mL) was added, the layers were separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The organic layers were combined, washed with saturated aqueous NaCl solution (100 mL), dried over magnesium sulfate and concentrated under reduced pressure to give an oil that was purified by flash column chromatography on silica gel eluting with 20% EtOAc/hexane to give the alcohols 12 (1.34 g), Rf0.5 (30% EtOAc/hexane), as a white foam which was used directly.

Provenance & Evidence