Tetrahydrofuran → Methyl 3-(3,5-difluorophenoxy)acrylate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[C:10]([O:14][CH3:15])(=[O:13])[C:11]#[CH:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>C(#N)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[O:9][CH:12]=[CH:11][C:10]([O:14][CH3:15])=[O:13]Participants
Procedure
A solution of 3,5-difluorophenol (35.5 g, 273 mmol) and methyl propiolate (25.0 mL, 300 mmol) in acetonitrile (109 mL) was added to a solution of tetrabutylammonium fluoride in tetrahydrofuran (1.0 M commercial solution, 109 mL, 109 mmol) at room temperature over a period of 2 hours. After complete addition of the solution, the mixture was stirred for 1 hour. The reaction mixture was diluted with toluene (350 mL) and the organic mixture was washed twice with water (250 mL×2), dried over magnesium sulfate, and concentrated in vacuum. The residue was purified by column chromatography on amino gel (hexane:ethyl acetate=3:2 as an eluent) to afford the title compound as a yellow solid (60.0 g, quant, 1:1 mixture of cis- and trans-isomers).
Workup
- additionAfter complete addition of the solution
- washthe organic mixture was washed twice with water (250 mL×2)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuum
- customThe residue was purified by column chromatography on amino gel (hexane
Sources & evidence
- ORD record
- ord-277d14b22a444c7a9e2c16c378a4866e
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723321B2
Reaction notes
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