5-(Difluoromethyl)furan-2-carbaldehyde → 2-Furanmethanol, 5-(difluoromethyl)-alpha-ethynyl-
Reaction equation
[C:1]([Mg]Br)#[CH:2].[F:5][CH:6]([F:14])[C:7]1[O:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=1.OP([O-])(O)=O.[Na+]>O1CCCC1>[F:5][CH:6]([F:14])[C:7]1[O:11][C:10]([CH:12]([OH:13])[C:1]#[CH:2])=[CH:9][CH:8]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
43 cm3 of a 0.5M solution of ethynyl magnesium bromide in tetrahydrofuran is added at 0° C. over one hour to a solution containing 2.5 g of the product prepared in Stage A and 30 cm3 of tetrahydrofuran. The reaction mixture is maintained under agitation at 0° C. for 1 hour. It is poured into a saturated aqueous solution of sodium acid phosphate. 3 g of product is obtained which is chromatographed on silica eluting with a hexane--ethyl acetate mixture (7-3). 2.5 g of desired product is obtained.
Sources & evidence
- ORD record
- ord-f2e40f6a9a4b4ce0a2aeb4da646cfc81
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05340835
Reaction notes
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