Water → methyl 3-(3-methyl-1-{3-(phenyl)propyl}-1H-indol-6-yl)-propenoate
Reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7](C=O)=[CH:8][CH:9]=2)[N:4]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:3]=1.[C:22]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:24][CH3:25])=[O:23].O.[C:47]1(C)C=CC=CC=1>>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:47]=[CH:26][C:22]([O:24][CH3:25])=[O:23])=[CH:8][CH:9]=2)[N:4]([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:3]=1Participants
5
Conditions
- Temperature
- 80 °C
Procedure
A stirred 3-methyl-1-{3-(phenyl)propyl}-1H-indole-6-carboxaldehyde (0.283 g, Reference Example 40) in dry toluene (20 ml), under argon, was treated with carbomethoxymethylene triphenylphosphorane (0.409 g). The mixture was heated at 80° C. for 4 hours then cooled to room temperature and then poured into water (20 ml). The organic phase was separated and the aqueous phase was extracted three times with ethyl acetate (30 ml). The combined organic phases were dried over magnesium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of diethyl ether and hexane (10:1, v/v) to yield the title compound (0.263 g).
Workup
- temperaturethen cooled to room temperature
- customThe organic phase was separated
- extractionthe aqueous phase was extracted three times with ethyl acetate (30 ml)
- dry with materialThe combined organic phases were dried over magnesium sulphate
- customthen evaporated
- additionThe residue was subjected to flash chromatography on silica eluting with a mixture of diethyl ether and hexane (10:1
Sources & evidence
- ORD record
- ord-f336a05ec08b40deadd5733efd12a3bc
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07329675B2
Reaction notes
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