Dimethyl Sulfoxide → 1-(2-Oxoethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

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Reaction Steps

Dimethylsulfoxide (0.35 mL, 5 mmol) and oxalyl chloride (2M in dichloromethane) (2.2 mL, 4.4 mmol) were stirred in dichloromethane (30 mL) under nitrogen at −78° C. After 10 min, 1-(2-hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile (0.48 g, 2.4 mmol) in dichloromethane (50 mL) was added dropwise and the solution stirred at −78° C. for 1 h, before triethylamine (2.5 mL, 18 mmol) was added slowly. The reaction was allowed to warm to room temperature and after 2 h the reaction was quenched by addition of water. Removal of the solvent in vacuo yielded the title compound, which was used in the next step without further purification.

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