Dimethyl Sulfoxide → HCID 86650335, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 19.04 g of oxalyl chloride in 200 mL of dichloromethane was cooled to −78° C. under a nitrogen atmosphere. To the solution was added dropwise a solution of 11.72 g of dimethyl sulfoxide in 50 mL of dichloromethane over 20 minutes, followed by stirring at −50° C. for 30 minutes. To the reaction mixture was added dropwise a solution of 22.83 g of 4-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]cyclohexanemethanol (trans/cis=6/4) in 50 mL of dichloromethane over 30 minutes, followed by stirring at −50° C. for 40 minutes. To the mixture was added dropwise 30.36 g of triethylamine over 40 minutes. The reaction mixture was stirred at room temperature for 18 hours. To the reaction mixture was added 100 mL of water. An organic layer was separated and then extracted twice with 100 mL of chloroform. The combined organic layer was washed sequentially with 150 mL of a 1 N aqueous hydrochloric acid solution, 150 mL of a saturated aqueous sodium hydrogen carbonate solution and then 150 mL of water, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 20.04 g of 4-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]cyclohexanecarbaldehyde represented by the following formula:

Provenance & Evidence