Ammonium Chloride → 3-(2,4,6-Trifluoro-phenyl)-acrylic acid ethyl ester

HRID 474577

反応式

HRID 474577 の反応式
[CH2:1]([O:3][C:4](=[O:12])[CH2:5]P(OC)(OC)=O)[CH3:2].CC([O-])(C)C.[K+].[F:19][C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:21]=1[CH:22]=O.[Cl-].[NH4+]>C1COCC1.CN(C=O)C.C1COCC1>[F:19][C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:21]=1/[CH:22]=[CH:5]/[C:4]([O:3][CH2:1][CH3:2])=[O:12]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 67555Ethyl (dimethoxyphosphinoyl)acetateHCID 5218452,4,6-TrifluorobenzaldehydeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 574127793-(2,4,6-Trifluoro-phenyl)-acrylic acid ethyl ester収率 87%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

実験手順

To the solution of ethyl[bis(methyloxy)phosphoryl]acetate (1.980 mL, 11.99 mmol) in THF-DMF (60 mL, v/v=5:1) at 0° C. was added t-BuOK (1.458 g, 12.99 mmol) portion wise. The resultant mixture was stirred at room temperature for 30 minutes, then mixed with a solution of 2,4,6-trifluorobenzaldehyde (1.6 g, 9.99 mmol) in THF (10 mL) at 0° C. It was allowed to warm to room temperature and the mixture was stirred for 45 min. It was mixed with aqueous ammonium chloride and then extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by a flash column chromatography to give the title compound as a pale yellow oil (2.0 g, 87% yield). LCMS: rt=3.52 min, [M+H+]=231.1

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by a flash column chromatography

出典と根拠

ORDレコード
ord-e0957e9540054c5f81479c9091b0c6c2
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

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