Dimethyl Sulfoxide → 2,3-Dihydro-1-benzofuran-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

DMSO (8.10 mL, 114 mmol) was added at -78° C. to a stirred solution of oxalyl chloride in CH2Cl2 (40 mL of a 2M solution). A solution of Part B 2,3-dihydrobenzofuran-4-methanol (8.53 g, 56.9 mmol) in CH2Cl2 (35 mL) was added dropwise, and the solution stirred at -78° C. for 30 min. Triethylamine (33 mL, 228 mmol) was added cautiously to quench the reaction. The resulting suspension was stirred at room temperature for 30 min. and diluted with CH2Cl2 (100 mL). The organic layer was washed three times with water, and twice with brine, and then concentrated in vacuo to give 2,3-dihydrobenzofuran-4-carboxaldehyde as an oil (8.42 g, 100%) that was used without purification.

Provenance & Evidence