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

HRID 474577

반응식

HRID 474577 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21974620tetrahydrofuran N,N-dimethylformamide용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-e0957e9540054c5f81479c9091b0c6c2
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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