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

HRID 350087Notes

Reaction equation

HRID 350087 reaction equation
[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

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 86760413HCID 86760413, compound

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-35f2b6181e414f1eb8e9d465ca4dcb9c
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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