Dimethylformamide → 4-{(Z)-2-[3-(benzyloxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole

HRID 2221541ノート

反応式

HRID 2221541 の反応式
[CH2:1]([O:8][C:9]1[C:13]([CH:14]=O)=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[S:23]1[CH:27]=[C:26]([CH2:28][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:25]=[CH:24]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:1]([O:8][C:9]1[C:13](/[CH:14]=[CH:28]\[C:26]2[N:25]=[CH:24][S:23][CH:27]=2)=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 22175328Triphenyl(1,3-thiazol-4-ylmethyl)phosphonium chlorideHCID 229307603-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 692156044-{(Z)-2-[3-(benzyloxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole収率 37.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 3-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde (1.70 g), [(1,3-thiazol-4-yl)methyl]triphenylphosphonium chloride (3.64 g), potassium carbonate (1.27 g) and N,N-dimethylformamide (100 mL) was stirred at room temperature for 15 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:3, v/v) to give 4-{(Z)-2-[3-(benzyloxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole as a colorless oil (0.82 g, yield 37%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (1:3

出典と根拠

ORDレコード
ord-f16cf242e6eb43789f45bbf76b536ad0
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

読み込み中…