Water → ethyl(E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoate

HRID 350322ノート

反応式

HRID 350322 の反応式
[H-].[Na+].[C:3]1([C:9]2[S:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:34]=[CH:33][C:19]([CH2:20][N:21]4[CH:25]=[C:24]([CH:26]=O)[C:23]([C:28]5[S:29][CH:30]=[CH:31][CH:32]=5)=[N:22]4)=[CH:18][CH:17]=3)[N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OP([CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])(OCC)=O)C.O>CN(C)C=O>[C:3]1([C:9]2[S:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:20][N:21]4[CH:25]=[C:24](/[CH:26]=[CH:43]/[C:44]([O:46][CH2:47][CH3:48])=[O:45])[C:23]([C:28]5[S:29][CH:30]=[CH:31][CH:32]=5)=[N:22]4)=[CH:33][CH:34]=3)[N:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 230247701-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 69423225ethyl(E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoate収率 93%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60%, oily, 150 mg) was added to a solution of 1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carbaldehyde (1.54 g) and ethyl diethylphosphonoacetate (0.82 g) in N,N-dimethylformamide (15 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed successively with dilute hydrochloric acid and saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl(E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoate (1.65 g, yield: 93%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1: 2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 104˜105° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with dilute hydrochloric acid and saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-20137f116219405d8b2b6ed11ac44ae0
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

反応ノート

読み込み中…