Dimethylformamide → 3-[(4-{[2-(2-furyl)-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 2221908Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[O:12][CH:13]=2)=[C:5]([O:21][CH3:22])[CH:4]=1.[OH:23][C:24]1[C:28]([CH:29]=[O:30])=[CH:27][N:26]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:25]=1.CN(C)C=O.[H-].[Na+]>O>[O:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[C:11]1[O:12][CH:13]=[C:9]([CH2:8][O:7][C:6]2[CH:19]=[CH:20][C:3]([CH2:2][O:23][C:24]3[C:28]([CH:29]=[O:30])=[CH:27][N:26]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:25]=3)=[CH:4][C:5]=2[O:21][CH3:22])[N:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-2-(2-furyl)-1,3-oxazole (0.80 g), 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde (0.45 g) and N,N-dimethylformamide (30 mL) was added sodium hydride (60% in oil, 0.10 g) at room temperature, and the mixture was stirred at 90° C. for 2 hrs. Water was added to the reaction mixture, and the precipitated crystals were collected by filtration to give 3-[(4-{[2-(2-furyl)-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde as pale-yellow crystals (0.93 g, yield 82%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 162-163° C.

Workup

filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-b0042f283b5a4b528aa0faec4d9ea207
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368578B2

Reaction notes

Loading…