Potassium Carbonate → Methyl 4-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate

HRID 1019029노트

반응식

HRID 1019029 반응식
[N:1]1([CH2:6][CH:7]=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[Br-].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]([CH:40]=[CH:41][C:42]=2[C:43]([O:45][CH3:46])=[O:44])[CH2:20][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[N:1]1([CH2:6][CH:7]=[CH:20][C:19]2[CH:40]=[CH:41][C:42]([C:43]([O:45][CH3:46])=[O:44])=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([F:10])=[CH:16][CH:15]=3)[CH:18]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 222385812-(1H-Imidazol-1-yl)acetaldehydeHCID 865903363-(4-Fluorophenyl)-4-methoxycarbonylbenzyl triphenylphosphonium bromide

생성물 1

HCID 54479740Methyl 4-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-(imidazol-1-yl)acetaldehyde (2.6 g; 0.018 mmol), 3-(4-fluorophenyl)-4-methoxycarbonylbenzyl triphenylphosphonium bromide (5.4 g; 0.09 mmol), potassium carbonate (1.38 g; 0.01 mmol) and 18 crown-6 (0.1 g; 0.37 mmol) in THF (150 ml) was stirred under argon atmosphere at ambient temperature overnight. After filtration of the insoluble material and evaporation to dryness, the residue was purified by flash chromatography eluting with a mixture of dichloromethane/ethanol (98/2) to give methyl 4-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate as a mixture of E and Z isomers. Yield: 93%.

후처리

  1. filtrationAfter filtration of the insoluble material and evaporation to dryness
  2. customthe residue was purified by flash chromatography
  3. washeluting with a mixture of dichloromethane/ethanol (98/2)

출처 및 근거

ORD 기록
ord-440c487169fd43bb8acbbedacfd84b9a
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486156B1

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