Triethyl phosphonoacetate → (2E)-3-(2,6-Difluoro-4-methoxyphenyl)-2-propenoic Acid Ethyl Ester

HRID 2110842ノート

反応式

HRID 2110842 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 57636644(2E)-3-(2,6-Difluoro-4-methoxyphenyl)-2-propenoic Acid Ethyl Ester収率 52.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-3054b3eb97e0463797f390fd5926faf9
出典データセット
uspto-grants-2009_04
特許番号
US07517910B2

反応ノート

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