Water → Z-4-(2-Fluoro-3-methoxyphenyl)-4-methylpent-2-enoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[Li+].CC([N-]C(C)C)C.[F:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=1[C:29]([CH3:33])([CH3:32])[CH:30]=O.O>C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C.O1CCCC1>[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:33]\[C:29]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:21]=1[F:20])([CH3:30])[CH3:32]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
20.26 g (111.26 mmol) of phosphonoacetic acid trimethyl ester is introduced into 68 ml of tetrahydrofuran. At 0° C., 61 ml of a 2 M solution of LDA in THF/heptane/ethylbenzene is added in drops. After 45 minutes of stirring, 21.83 g (111.26 mmol) of 2-(2-fluoro-3-methoxyphenyl)-2-methylpropanal, dissolved in 68 ml of tetrahydrofuran, is added in drops at 0° C. After stirring overnight, the reaction mixture is mixed with water while being cooled in an ice bath, and it is extracted three times with methyl tert-butyl ether. The combined organic extracts are treated as usual, and the residue that is obtained is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 23.30 g (75.8%) of the desired compound is isolated.
Workup
- additionis added in drops at 0° C
- stirringAfter stirring overnight
- temperaturewhile being cooled in an ice bath
- extractionit is extracted three times with methyl tert-butyl ether
- additionThe combined organic extracts are treated as usual, and the residue that
- customis obtained
- customis chromatographed on silica gel (mobile solvent ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-589dce2ec4e04350923b0ee0cee19e20
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638515B2
Reaction notes
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