Dimethyl Sulfoxide → Ethyl 4-(1-oxaspiro[2.5]oct-6-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

0.246 g of sodium hydride (9.74 mmol, 2 eq.) is placed in 25 mL of a 1/1.5 mixture of THF/DMSO with stirring at 10° C. 2.14 g of trimethylsulfoxonium iodide (9.74 mmol, 1.2 eq.) are added. After 5 minutes, 10 mL of DMSO are added dropwise. After the evolution of gas has ceased, 2 g of ethyl 4-(4-oxocyclohexyl)benzoate (8.12 mmol, 1 eq.) dissolved in a minimum amount of a 2/1 mixture of DMSO/THF are rapidly added at room temperature. After stirring for 1 hour at room temperature and for 1 hour at 50° C., the reaction medium is diluted with 75 mL of water and extracted with ethyl acetate. The organic phases are successively washed twice with water and with brine, dried over sodium sulfate and evaporated. The residue is chromatographed on silica gel with a gradient of methanol in dichloromethane ranging from 1% to 2%. 1.8 g of ethyl 4-(1-oxaspiro[2.5]oct-6-yl)benzoate are obtained.

Provenance & Evidence