Water → 4-[2-Hydroxy-5-(2-methyl-[1,3]dioxolan-2-yl)-pentyloxy]-7a-methyl-hexahydro-indene-1,5-dione

Participants

Reaction Conditions

Reaction Steps

Potassium iodide (31.1 g, 187.5 mmol, 3 eq) was added to a solution of 2-(3-chloro-propyl)-2-methyl-[1,3]dioxolane (18.8 mL, 125 mmol, 2 eq) in DMF (50 mL) and the reaction mixture was stirred at 60° C. in dark for 6 h. The reaction mixture was then cooled to room temperature and then combined with (7a-Methyl-1,5-dioxo-octahydro-inden-4-yloxy)-acetaldehyde (14 g, 62.5 mmol) in DMF (150 mL). To the stirred mixture at 0° C., was added cobalt phthalocyanine (357 mg, 0.625 mmol, 0.01 eq), followed by chromous chloride (23.1 g, 187.5 mmol, 3 eq) portion-wise, resulting in release of heat. The reaction mixture was allowed to stir from 0° C. slowly to room temperature for 24 h. The reaction mixture was then cooled to 0° C. and cold water (200 mL) was added. The resulting mixture was extracted with pentane (200 mL). The aqueous layer was extracted with dichloromethane (4×200 mL). The combined organic layer was dried with magnesium sulfate, filtered, the solvent was removed together with toluene (2×100 mL) under reduced pressure, and the resulting residue purified by flash chromatography 20-70% ethyl acetate in hexane to yield the tile compound as an oil, as 1:1 mixture of two diastereomers.

Provenance & Evidence