Dimethyl Sulfoxide → 2-(2-(2,2,2-Trifluoroethoxy)phenoxy)acetaldehyde

Participants

Reaction Steps

A solution of oxalyl chloride (0.73 ml, 8 mmole) in Dichloromethane (7 ml) was cooled below −70° C. Then charged DMSO (1.2 ml) below −70° C. To the reaction mixture was added, solution of 2-[2-(2,2,2-Trifluoro-ethoxy)-phenoxy]-ethanol (XIV) (1.0 g, 4 mmole) in Dichloromethane (10 ml) over a period of 10 minutes below −50° C. Triethylamine (2.3 ml, 0.016 mole) was added below −70° C. Reaction mixture was quenched in cold water and the product was extracted with Dichloromethane (10 ml). Organic layer was washed with aqueous sodium bicarbonate solution followed by washing with water. Dried the organic layer over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (5/95) as eluent to give 0.6 g of (VIII) as colourless solid, melting at 57-58° C.

Provenance & Evidence