Dimethyl Sulfoxide → HCID 17989289, compound

Participants

Reaction Steps

6.15 g (20.45 mmol) of ethyl 4-(4-chloro-3-methoxyphenyl)-2-hydroxy-4-methyl-pentanoate is dissolved in 213 ml of dichloromethane and mixed with 71 ml of dimethyl sulfoxide. After 10.3 g (102.23 mmol) of triethylamine is added, the batch is mixed in portions with 8.1 g (51.12 mmol) of SO3/pyridine complex and then stirred overnight at room temperature. The reaction mixture is mixed while being cooled slightly with 81 ml of saturated ammonium chloride solution and vigorously stirred. After 2× extraction with diethyl ether, the combined organic phases are treated as usual. The residue that remains after the solvent is spun off is chromatographed on silica gel (mobile solvent ethyl acetate/hexane) together with the residue that results from another batch (15.27 g). 15.46 g (72.9%, from the two batches) of the desired compound is isolated.

Provenance & Evidence