3,5-Dichloro-1-methylpyrazole-4-carbonyl chloride → 2-{2-Tert-butyloxazol-4-yl}-3-(3,5-dichloro-1-methyl-pyrazol-4-yl)-3-hydroxyacrylonitrile

HRID 230092노트

반응식

HRID 230092 반응식
CC(C)([O-])C.[K+].[C:7]([C:11]1[O:12][CH:13]=[C:14]([CH2:16][C:17]#[N:18])[N:15]=1)([CH3:10])([CH3:9])[CH3:8].[Cl:19][C:20]1[C:24]([C:25](Cl)=[O:26])=[C:23]([Cl:28])[N:22]([CH3:29])[N:21]=1>C1COCC1>[C:7]([C:11]1[O:12][CH:13]=[C:14]([C:16](=[C:25]([C:24]2[C:20]([Cl:19])=[N:21][N:22]([CH3:29])[C:23]=2[Cl:28])[OH:26])[C:17]#[N:18])[N:15]=1)([CH3:10])([CH3:8])[CH3:9]

참가 물질

5

반응물 3

HCID 221694993,5-Dichloro-1-methylpyrazole-4-carbonyl chlorideHCID 221695172-(2-tert-Butyl-1,3-oxazol-4-yl)acetonitrileHCID 23665647Potassium tert-butoxide

생성물 1

HCID 572553782-{2-Tert-butyloxazol-4-yl}-3-(3,5-dichloro-1-methyl-pyrazol-4-yl)-3-hydroxyacrylonitrile수율 86.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2.87 g of potassium tert-butoxide was suspended in 20 ml of THF, and a solution of 2.00 g of 2-tert-butyl-4-cyanomethyloxazole and 2.37 g of 3,5-dichloro-1-methylpyrazole-4-carbonyl chloride as dissolved in 10 ml of THF was dropwise added thereto with cooling with ice, and then stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed with a small amount of water. After the resulting product was dried with anhydrous sodium sulfate, the solvent was evaporated out under reduced pressure. The residual product was purified through column chromatography (silica gel; n-hexane:ethyl acetate=4:1) to obtain 3.26 g of the intended compound.

후처리

  1. additionwas dropwise added
  2. temperaturewith cooling with ice
  3. extractionextracted with ethyl acetate
  4. washwashed with a small amount of water
  5. dry with materialAfter the resulting product was dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated out under reduced pressure
  7. customThe residual product was purified through column chromatography (silica gel; n-hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-d4ad6206a74644a9b75f7a6b4d70b62d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566683B2

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