Dimethyl Sulfoxide → HCID 178501146, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (4.48 mL) in methylene chloride (50 mL) is added dropwise dimethylsulfoxide (4.55 g) in methylene chloride (5 mL) at −60° C. over a period of 15 minutes. To the mixture is added dropwise a solution of methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (compound obtained in Reference Example 238; 5.9 g) in methylene chloride (30 mL) over a period of 30 minutes. The mixture is stirred at the same temperature for 1 hour and thereto is added dropwise triethylamine (16.7 mL) at −60° C. The mixture is stirred at the same temperature for 30 minutes and at 0° C. for 1 hour. The reaction mixture is diluted with chloroform, and washed successively with water, 5% citric acid solution, water, and saturated brine. The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo to give methyl trans-4-formylcyclohexanecarboxylate (5.32 g, yield; 91%) as an oil.

Provenance & Evidence