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

HRID 1019029ノート

反応式

HRID 1019029 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-440c487169fd43bb8acbbedacfd84b9a
出典データセット
uspto-grants-2002_11
特許番号
US06486156B1

反応ノート

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