Dimethylformamide → ethyl 3-({6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methoxy)-1-phenyl-1H-pyrazole-4-carboxylate

HRID 2221776Notes

Reaction equation

Cl[CH2:2][C:3]1[O:4][C:5]2[CH:17]=[C:16]([O:18][CH2:19][C:20]3[N:21]=[C:22]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:23][C:24]=3[CH3:25])[CH:15]=[CH:14][C:6]=2[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:32][C:33]1[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:36][N:35]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:34]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:25][C:24]1[O:23][C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:21][C:20]=1[CH2:19][O:18][C:16]1[CH:15]=[CH:14][C:6]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:3]([CH2:2][O:32][C:33]3[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:36][N:35]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[N:34]=3)[O:4][C:5]=2[CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-({[2-(chloromethyl)-3-phenyl-1-benzofuran-6-yl]oxy}methyl)-5-methyl-2-phenyl-1,3-oxazole (1.16 g), ethyl 3-hydroxy-1-phenyl-1H-pyrazole-4-carboxylate (0.58 g), potassium carbonate (0.35 g) and N,N-dimethylformamide (30 mL) was stirred at 90° C. for 3 hrs. Water was poured into the reaction mixture, and the precipitated crystals were collected by filtration, and subjected to silica gel column chromatography to give ethyl 3-({6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methoxy)-1-phenyl-1H-pyrazole-4-carboxylate as colorless crystals (1.19 g, 76%) from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 143-144° C.

Workup

filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-a071e5f2869a4c7fb7a1b89e4d33f904
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368578B2

Reaction notes

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