Water → (E)-tert-Butyl 3-(pyridin-2-yl)acrylate
Reaction equation
[H-].[Na+].C(P([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])CC)C.[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=O.O>CCCCCC.O1CCCC1>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1/[CH:16]=[CH:8]/[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10]Participants
Procedure
Sodium hydride (60% oil, 0.6 g, 15.7 mmol) was washed with hexane and suspended in tetrahydrofuran (5 ml). To the mixture, a solution of tert-butyl diethylphosphinoacetate (2.5 g, 9.8 mmol) in tetrahydrofuran (2 ml) was added under ice cooling condition. The reaction mixture was stirred at room temperature for 30 minutes, cooled under ice cooling condition. A solution of 2-formylpyridine (1.0 g, 9.3 mmol) in tetrahydrofuran (3.0 ml) was added to the mixture, and the mixture was stirred at 0° C. for 1.5 hrs. The reaction mixture was combined with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to a silica gel (60 g) column chromatography, and eluted with hexane-ethyl acetate (3:1, v/v) to give the titled compound (1.5 g, 77%).
Workup
- temperaturecooled under ice cooling condition
- stirringthe mixture was stirred at 0° C. for 1.5 hrs
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- washeluted with hexane-ethyl acetate (3:1
Sources & evidence
- ORD record
- ord-28847c0507294ccb9a1f02c51bf5afea
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767665B2
Reaction notes
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