Methanol → (3,3-Diphenylpropane-1-yl)3-oxo-4-(2-(pyridine-2-yl)ethoxy)butanoate
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][OH:9].[H-].[Na+].[C:12]1([CH:18]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:19][CH2:20][O:21][C:22](=[O:28])[CH2:23][C:24]([CH2:26]Cl)=[O:25])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO>C1COCC1>[C:12]1([CH:18]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:19][CH2:20][O:21][C:22](=[O:28])[CH2:23][C:24](=[O:25])[CH2:26][O:9][CH2:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
6
Procedure
503 mg (4.08 mmol) of 2-(pyridine-2-yl)ethanol was added dropwise to a suspension of 326 mg (8.16 mmol) of sodium hydride (60% oily) in 10 ml of THF at 0° C., and they were stirred for 30 minutes. A solution of 0.90 mg (2.72 mmol) of (3,3-diphenylpropane-1-yl)4-chloroacetoacetate in 3 ml of THF was added dropwise to the reaction mixture, and they were stirred at room temperature overnight. After the addition of methanol, the reaction mixture was concentrated and fractionated with ethyl acetate and water. After the drying over sodium sulfate followed by the purification by the silica gel chromatography (methylene chloride/methanol=100/1), the title compound was obtained.
Workup
- stirringwere stirred at room temperature overnight
- concentrationthe reaction mixture was concentrated
- customAfter the drying over sodium sulfate followed by the purification by the silica gel chromatography (methylene chloride/methanol=100/1)
Sources & evidence
- ORD record
- ord-4186a5932c13481ea2bf3c30eac1e6cd
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07247645B2
Reaction notes
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