Water → ethyl(E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-(2-pyridyl)-3-pyrrolyl]propenoate

HRID 350087ノート

反応式

HRID 350087 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][C:18]1[O:22][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:20][C:19]=1[CH2:29][O:30][C:31]1[CH:50]=[CH:49][C:34]([CH2:35][N:36]2[CH:40]=[C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43]C=3)[C:38]([CH:47]=O)=[CH:37]2)=[CH:33][CH:32]=1.O.C[N:53](C)C=O>>[CH3:17][C:18]1[O:22][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:20][C:19]=1[CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:35][N:36]2[CH:40]=[C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:53]=3)[C:38](/[CH:47]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:37]2)=[CH:49][CH:50]=1

参加物

6

反応物 5

HCID 962WaterHCID 6228Dimethylformamide2 回HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 86760413HCID 86760413、化合物

生成物 1

HCID 69420181ethyl(E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-(2-pyridyl)-3-pyrrolyl]propenoate収率 96%

実験手順

Sodium hydride (60%, oily, 0.17 g) was added to a mixture of ethyl diethylphosphonoacetate (1.00 g) and N,N-dimethylformamide (5 ml) at 0° C., and the mixture was stirred at room temperature for 30 minutes. A solution of 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-phenylpyrrole-3-carbaldehyde (1.65° g) in N,N-dimethylformamide (10 ml) was added slowly to the mixture, which was stirred at room temperature for 3 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatograpy, and ethyl(E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-(2-pyridyl)-3-pyrrolyl]propenoate (1.83 g, yield: 96%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:1 volume ratio).

後処理

  1. stirringwas stirred at room temperature for 3 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-35f2b6181e414f1eb8e9d465ca4dcb9c
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…