Triethyl phosphonoacetate → HCID 57636644, compound

HRID 2110842Notes

Reaction equation

HRID 2110842 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[F:17][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([F:28])[C:19]=1[CH:20]=O>O1CCCC1.C(OCC)(=O)C>[F:17][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([F:28])[C:19]=1/[CH:20]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 37037132,6-Difluoro-4-methoxybenzaldehyde

Product 1

HCID 57636644HCID 57636644, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl diethylphosphonoacetate (2.34 g, 10.4 mmol) and sodium hydride (60% in oil, 0.38 g, 9.50 mmol) in tetrahydrofuran (40 mL) was stirred under ice-cooling for 10 min. 2,6-Difluoro-4-methoxybenzaldehyde (1.5 g, 8.71 mmol) was added to the solution, and the mixture was stirred for 4 hr while raising the temperature to room temperature. The reaction mixture was diluted with ethyl acetate, and the mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (1.1 g, yield 52%) as colorless needle crystals. MS: m/z 243 (MH+).

Workup

  1. temperaturecooling for 10 min
  2. washthe mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3054b3eb97e0463797f390fd5926faf9
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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