Water → ethyl(E)-3-[1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-4-phenyl-3-pyrrolyl]propenoate

HRID 350263Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[N:22]=[CH:21][C:20]([CH2:23][N:24]2[CH:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:26]([CH:35]=O)=[CH:25]2)=[CH:19][CH:18]=1.C(OP([CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])(OCC)=O)C.O>CN(C)C=O>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[N:22]=[CH:21][C:20]([CH2:23][N:24]2[CH:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:26](/[CH:35]=[CH:45]/[C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:25]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60%, oily, 190 mg) was added to a solution of 1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-4-phenyl-3-pyrrolecarbaldehyde (1.05 g) and ethyl diethylphosphonoacetate (1.05 g) in N,N-dimethylformamide (50 ml) at 0° C., and the mixture was stirred at 0° C. for 2 hours. The reaction mixture was poured into water, and the precipitated crystals were collected by filtration to obtain ethyl(E)-3-[1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-4-phenyl-3-pyrrolyl]propenoate. The crystals were dissolved in ethanol (80 ml), and hydrogenated on 5% palladium-carbon (800 mg) at room temperature under a normal pressure. The catalyst was filtered, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 3-[1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-4-phenyl-3-pyrrolyl]propionate (1.05 g, yield: 86%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:2, volume 5 ratio).

Workup

filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-8bcfe06610f44897b5840b47c29887ab
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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