Methyl cyanoacetate → 2-Cyano-3-methyl-4-oxo-4-(2-trifluoromethyl-phenyl)-butyric acid methyl ester

HRID 912577노트

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HRID 912577 반응식
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:4].Br[CH:11]([CH3:24])[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:22])[F:21])=[O:13]>C1COCC1>[CH3:9][O:8][C:6](=[O:7])[CH:5]([C:3]#[N:4])[CH:11]([CH3:24])[C:12](=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:21])([F:22])[F:23]

참가 물질

5

반응물 3

HCID 7747Methyl cyanoacetateHCID 24758Sodium hydrideHCID 201874742-Bromo-1-[2-(trifluoromethyl)phenyl]propan-1-one

생성물 1

HCID 598075352-Cyano-3-methyl-4-oxo-4-(2-trifluoromethyl-phenyl)-butyric acid methyl ester수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
20 °C

실험 절차

To a suspension of NaH (60%, 2.88 g, 72 mmol) in anhyd THF (200 mL) was added methyl cyanoacetate (4.5 mL, 50 mmol). After this mixture was stirred for 3 h at 20° C., a solution of 2-bromo-1-(2-trifluoromethyl-phenyl)-propan-1-one (13.5 g, 48 mmol) was added and the mixture was stirred overnight at 20° C. The mixture was quenched with water and the organic layer was separated. The aqueous layer was extracted with EtOAc. The combined extracts were washed with brine, dried (anhyd Na2SO4) and concentrated under reduced pressure to afford the title compound as an oil (13.3 g, 93%), which was used in the next step without purification. MS (ES): 300 (MH+).

후처리

  1. stirringthe mixture was stirred overnight at 20° C
  2. customThe mixture was quenched with water
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (anhyd Na2SO4)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a3a00388fd38447484558a00fb642afc
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026237B2

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