Dimethylformamide → 4-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-(methoxymethoxy)benzaldehyde

HRID 2221519Notes

Reaction equation

HRID 2221519 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].[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][C:16]=1[O:23][CH2:24][O:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:5]1[O:6][C:7]([CH3:8])=[C:3]([CH2:2][O:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][C:16]=2[O:23][CH2:24][O:25][CH3:26])[N:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12397043HCID 12397043, compoundHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

Product 1

HCID 230766164-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-(methoxymethoxy)benzaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-chloromethyl-2-(2-furyl)-5-methyl-1,3-oxazole (13.12 g), 4-hydroxy-3-methoxymethoxybenzaldehyde (11.0 g), potassium carbonate (8.35 g) and N,N-dimethylformamide (200 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 dried to give 4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-(methoxymethoxy)benzaldehyde as pale-brown crystals (16.11 g, yield 78%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 102-103° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-98f09afa15c842818aea093b00466ed3
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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