Diethyl Ether → HCID 178491319, compound

HRID 423186Notes

Reaction equation

HRID 423186 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([CH2:9][C:10](=[O:15])[C:11]([O:13]C)=O)=[O:8])=[CH:5][CH:4]=1.[O:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)=[N:19]1.[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH:34]=O.C(OCC)C>O1CCOCC1>[F:30][C:31]1[CH:32]=[C:33]([CH:34]2[N:27]([C:26]3[CH:28]=[CH:29][C:23]([C:20]4[CH:21]=[CH:22][O:18][N:19]=4)=[CH:24][CH:25]=3)[C:11](=[O:13])[C:10]([OH:15])=[C:9]2[C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=2)[CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 680093-FluorobenzaldehydeHCID 308121methyl 4-(4-methoxyphenyl)-2,4-dioxobutanoateHCID 231185764-(1,2-Oxazol-3-yl)aniline

Product 1

HCID 178491319HCID 178491319, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of methyl (4-methoxybenzoyl)pyruvate (0.24 g, 1 mmol) and 4-isoxazol-3-ylaniline (0.16 g, 1 mmol) in dioxane (1 mL) was added 3-fluorobenzaldehyde (0.11 mL, 1 mmol). The mixture was stirred at r.t. for two days. Diethyl ether (3 mL) was then added to the mixture, and the precipitate was collected by filtration to give 5-(3-fluorophenyl)-3-hydroxy-1-(4-isoxazol-3-ylphenyl)-4-(4-methoxybenzoyl)-1,5-dihydropyrrol-2-one (0.16 g, 34%) as slightly yellow crystals.

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-282121cb74ed4ad1b2536a0124ceb838
Source dataset
uspto-grants-2012_01
Patent number
US08101644B2

Reaction notes

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