Dimethyl Sulfoxide → 5-(Difluoromethyl)furan-2-carbaldehyde
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][CH:12]([F:20])[C:13]1[O:17][C:16]([CH2:18][OH:19])=[CH:15][CH:14]=1.OP([O-])(O)=O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[F:11][CH:12]([F:20])[C:13]1[O:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -60 °C
Procedure
A solution containing 6.5 cm3 of DMSO (dimethyl sulphoxide) and 60 cm3 of methylene chloride is added at -60° C. under a nitrogen atmosphere to a solution containing 3.84 cm3 of oxalyl chloride and 40 cm3 of methylene chloride. The reaction mixture is maintained under agitation at -60° C. and 3.6 g of 5-difluoromethyl 2-furanmethanol in solution in 30 cm3 of methylene chloride is added. Agitation takes place for 2 hours at -60° C. and a solution of 16.1 cm3 of triethylamine and 30 cm3 of methylene chloride is added over 15 minutes. The reaction mixture is maintained under agitation for half an hour at -60° C., then the temperature is allowed to rise to -20° C. and agitation is continued at this temperature for half an hour. It is poured into a solution of sodium acid phosphate, extracted with methylene chloride and dried. 3.6 g of product is obtained which is chromatographed on silica eluting with a hexane--ethyl-acetate mixture 8-2. After chromatography 2.5 g of desired product is obtained.
Workup
- additionis added at -60° C. under a nitrogen atmosphere to a solution
- customfor 2 hours
- customat -60° C.
- temperatureThe reaction mixture is maintained under agitation for half an hour at -60° C.
- customto rise to -20° C.
- waitagitation is continued at this temperature for half an hour
- extractionextracted with methylene chloride
- customdried
Sources & evidence
- ORD record
- ord-f163b09db818475e885314bac1937210
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05340835
Reaction notes
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