Dimethyl Sulfoxide → HCID 86702733, compound

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Reaction Steps

At −78° C., 1.31 g (16.8 mmol) of dimethyl sulphoxide are slowly added dropwise to 1.067 g (8.4 mmol) of oxalyl chloride in 40 ml of dichloromethane, and the mixture is stirred at this temperature for 20 min. 1.70 g (4.20 mmol) of 3-(benzyloxy)-2-(2,6-diethyl-4-methylphenyl)-5-(hydroxymethyl)-4,5,6,6a-tetrahydropentalen-1(3aH)-one (Example I-a-1), dissolved in 30 ml of dichloromethane, are then slowly added dropwise, and the mixture is stirred for another hour. 2.13 g (21 mmol) of triethylamine are then added slowly, and the mixture is brought to room temperature. Addition of 50 ml of saturated ammonium chloride solution, separation, washing of the organic phase with water, drying (magnesium sulphate), concentration on a rotary evaporator and chromatographic purification of the resulting crude product on silica gel (mobile phase ethyl acetate/hexane 1:5) gives 1.24 g (73%) of the title compound as a colourless oil.

Provenance & Evidence