(3,4-Difluorophenyl)acetonitrile → HCID 14838784, 화합물

HRID 1525575노트

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HRID 1525575 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[F:8].[F:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]([O:23][CH3:24])=[O:22])[CH:16]=[CH:17][CH:18]=1>C1(C)C=CC=CC=1.CC(C)([O-])C.[K+]>[C:10]([CH:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[CH:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([F:12])[CH:14]=1)[CH2:20][C:21]([O:23][CH3:24])=[O:22])#[N:11]

참가 물질

5

반응물 2

HCID 69572(3,4-Difluorophenyl)acetonitrileHCID 53395455Methyl 3-fluorocinnamate

생성물 1

HCID 14838784HCID 14838784, 화합물수율 96.5%

시약·촉매·용매 2

HCID 23665647Potassium tert-butoxide촉매HCID 1140Toluene용매

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온도
65 °C

실험 절차

Under protective gas (Ar), 3.828 g (25.0 mmol) of (3,4-difluorophenyl)acetonitrile and 0.281 mg of potassium tert-butoxide were added to 4.099 g (22.7 mmol) of methyl 3-(3-fluorophenyl)acrylate in 25.0 ml of toluene, and the mixture was stirred in a closed vessel at 65° C. for 5 h. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel (ethyl acetate/heptane=20:80) gave 7.3 g (87% of theory) of the diastereomeric methyl 4-cyano-4-(3,4-difluorophenyl)-3-(3-fluorophenyl)butanoate (erythro:threo=65:35 according to integration of the methyl singlets in the 1H-NMR in CDCl3 at 3.68 and 3.59 ppm).

후처리

  1. customThe solvent was removed under reduced pressure
  2. washthe mixture was washed twice with in each case 25 ml of water
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-e8affb76ef4c4349879bc781c10d1e72
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09084425B2

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