5-Acetoxymethyl-2-furaldehyde → (5-(Difluoromethyl)furan-2-yl)methyl acetate
Reaction equation
[F-:1].[F-:2].[F-].C(N(SN(CC)CC)CC)C.[C:15]([O:18][CH2:19][C:20]1[O:24][C:23]([CH:25]=O)=[CH:22][CH:21]=1)(=[O:17])[CH3:16].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:15]([O:18][CH2:19][C:20]1[O:24][C:23]([CH:25]([F:2])[F:1])=[CH:22][CH:21]=1)(=[O:17])[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution containing 7.26 cm3 of DAST (diethylamino sulphide trifluoride) and 30 cm3 of methylene chloride is added at 5° C. to a solution containing 10 g of the product prepared in Stage A and 100 cm3 of methylene chloride. The reaction mixture is agitated at 20° C. for half an hour and is taken to reflux for 1 hour. It is maintained under agitation for 18 hours at 20° C. and taken to reflux for 3 hours, then treated with sodium acid carbonate and extracted with methylene chloride. After drying and concentrating, 12 g of a product is obtained which is chromatographed on silica eluting with a hexane--ethyl acetate mixture (8-2). In this way 5.5 g of desired product is obtained.
Workup
- additionis added at 5° C. to a solution
- temperatureto reflux for 1 hour
- temperatureIt is maintained under agitation for 18 hours at 20° C.
- temperatureto reflux for 3 hours
- extractionextracted with methylene chloride
- customAfter drying
- concentrationconcentrating
Sources & evidence
- ORD record
- ord-5df6aa9b0e414827bfaf4f67c3520eee
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05340835
Reaction notes
Loading…