Reaction equation
[H-].[Na+].[CH3:3][CH2:4][CH:5](P(OCC)(OCC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:19][NH:20][C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:19][NH:20][C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][C:30](/[CH:33]=[C:5](\[CH2:4][CH3:3])/[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
197 mg (4.9 mmol) of sodium hydride are added to a mixture of 1.2 mL (4.9 mmol) of triethyl 2-phosphonobutyrate and 415 mg of 3′-methylaminobiphenyl-4-carbaldehyde (2.0 mmol) in 10 mL of tetrahydrofuran. The reaction mixture is stirred at room temperature overnight, poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is evaporated off and the residue (1.1 g) is purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 438 mg (72%) of ethyl 2-[1-(3′-methylaminobiphenyl-4-yl)meth-(E)-ylidene]butyrate are obtained in the form of off-white crystals.
Workup
- extractionextracted with ethyl acetate
- washwashed with water
- dry with materialdried over sodium sulfate
- customThe solvent is evaporated off
- customthe residue (1.1 g) is purified by chromatography on a column of silica
- washeluted with a 90/10 heptane/ethyl acetate mixture
Sources & evidence
- ORD record
- ord-919b2e7b34d54fd6b60e8686154cb1ac
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383652B2
Linked notes
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