Dimethyl Sulfoxide → 5-(Difluoromethyl)furan-2-carbaldehyde

Temperature

-60 °C

A solution of 6.5 ml of DMSO (dimethyl sulfoxide) and 60 ml of methylene chloride was added at -60° C. under a nitrogen atmosphere to a solution of 3.84 ml of oxalyl chloride and 40 ml of methylene chloride. The reaction mixture was stirred at -60° C. and 3.6 g of 5-difluoromethyl,2-furanmethanol in solution in 30 ml of methylene chloride were added. The mixture was stirred for 2 hours at -60° C. and a solution of 16.1 ml of triethylamine and 30 ml of methylene chloride was added over 15 minutes. The reaction mixture was stirred for half an hour at -60° C., the temperature was allowed to rise to -20° C. The mixture was stirred for half an hour at this temperature and then poured into a solution of sodium dihydrogenphosphate and extracted with methylene chloride. The extract was dried and the 3.6 g of product were chromatographed on silica by eluting with an 8/2 hexane/ethyl acetate mixture to obtain after chromatography, 2.5 g of the desired product.

1. stirringThe mixture was stirred for 2 hours at -60° C.
2. stirringThe reaction mixture was stirred for half an hour at -60° C.
3. customto rise to -20° C
4. stirringThe mixture was stirred for half an hour at this temperature
5. extractionextracted with methylene chloride
6. customThe extract was dried
7. customthe 3.6 g of product were chromatographed on silica
8. washby eluting with an 8/2 hexane/ethyl acetate mixture

ORD record

ord-da217df111a54be78bd7dfb445597b71

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05405865