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

HRID 732183ノート

反応式

HRID 732183 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 60% sodium hydride (0.38 g, 9.50 mmol) in tetrahydrofuran (40 mL) was stirred under ice-cooling for 10 min. Thereto was added 2,6-difluoro-4-methoxybenzaldehyde (1.5 g, 8.71 mmol) and the mixture was stirred for 4 hr while allowing to warm to room temperature. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (1.1 g, yield 52%) as colorless needles.

後処理

  1. temperaturecooling for 10 min
  2. washwashed successively with aqueous citric acid solution, water and aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=1:10-1:5)

出典と根拠

ORDレコード
ord-fdbfe1ac536849b2971a7de07583612c
出典データセット
uspto-grants-2009_09
特許番号
US07585880B2

反応ノート

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