Dimethylformamide → HCID 85954512, compound

HRID 2221510Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8].[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[OH:25])[CH:20]=[O:21])[CH3:15].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8])[CH:20]=[O:21])[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-chloromethyl-2-(2-furyl)-5-methyl-1,3-oxazole (30.0 g), 3-ethoxy-4-hydroxybenzaldehyde (22.9 g), potassium carbonate (21.01 g) and N,N-dimethylformamide (300 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the precipitated crystals were collected by filtration to give 3-ethoxy-4-[[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy]benzaldehyde as brown crystals (31.20 g, yield 69%). Recrystallization from ethyl acetate-hexane gave pale-yellow needle. melting point: 159-160° C.

Workup

filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-3c66ffe3fbfd46eda770ec45ac074bd1
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368578B2

Reaction notes

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