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

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.

1. additionTo the reaction mixture was added
2. customReaction mixture
3. customwas quenched in cold water
4. extractionthe product was extracted with Dichloromethane (10 ml)
5. washOrganic layer was washed with aqueous sodium bicarbonate solution
6. washby washing with water
7. dry with materialDried the organic layer over sodium sulphate
8. customThe solvent was evaporated under reduced pressure
9. customthe residue was purified by column chromatography on silica gel using
10. additiona mixture of ethyl acetate and hexane (5/95) as eluent

ORD record

ord-c212f4c153fa4779901d446e2cabff3a

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08471039B2