Sodium hydride → HCID 73804349, compound
Reaction equation
[H-].[Na+].CC(P(OC)(O)=O)(C([O-])=O)C.[F:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH:17]=O.[C:25]([CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:27][CH2:28]C)=[O:26].[Cl-].[NH4+]>O1CCCC1>[CH3:28][O:27][C:25](=[O:26])[CH:30]=[CH:17][C:16]1[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=1[F:14]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydride (60% in mineral oil, 3.11 g, 77.86 mmol) is suspended in dry tetrahydrofuran (160 mL) and cooled to 0° C. Trimethylphosphonoacetate (14.18 g, 77.86 mmol) is added and the mixture stirred at 0° C. for 30 minutes. 2-Fluoro-4-methoxybenzaldehyde (10 g, 64.88 mmol) is added and the mixture stirred overnight at room temperature. (Carbethoxymethylene)triphenylphosphorane (11.3 g, 32.44 mmol) is added and the mixture stirred for 3 hours. Saturated aqueous ammonium chloride solution is added and the mixture extracted with ethyl acetate. The organic phase is dried and the solvent removed under vacuum. The residue is purified by flash chromatography (5% ethyl acetate in cyclohexane) to give the title compound (yield 13.85 g).
Workup
- stirringthe mixture stirred overnight at room temperature
- stirringthe mixture stirred for 3 hours
- extractionthe mixture extracted with ethyl acetate
- customThe organic phase is dried
- customthe solvent removed under vacuum
- customThe residue is purified by flash chromatography (5% ethyl acetate in cyclohexane)
Sources & evidence
- ORD record
- ord-bb068f98d6c24eb0b2a2f5092be9ae3f
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633182B2
Reaction notes
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