4-Hydroxybenzaldehyde → 4-[(2-Phenyl-5-propyl-4-oxazolyl)methoxy]benzaldehyde

HRID 1294163Notes

Reaction equation

HRID 1294163 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6][C:7]=1[CH2:8][CH2:9][CH3:10].[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:11]1([C:5]2[O:6][C:7]([CH2:8][CH2:9][CH3:10])=[C:3]([CH2:2][O:17][C:18]3[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=3)[N:4]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 178613954-Chloromethyl-2-phenyl-5-propyloxazole

Product 1

HCID 865915624-[(2-Phenyl-5-propyl-4-oxazolyl)methoxy]benzaldehydeYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-chloromethyl-2-phenyl-5-propyloxazole (2.26 g), 4-hydroxybenzaldehyde (1.33 g), anhydrous potassium carbonate (1.76 g) and N,N-dimethylformamide (50 mL) was stirred at 60° C. for 4 hrs. The reaction mixture was poured into water, and the precipitated solid was collected by filtration and dried with air to give crystals (2.75 g, 89%) of 4-[(2-phenyl-5-propyl-4-oxazolyl)methoxy]benzaldehyde. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 76-77° C.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried with air

Sources & evidence

ORD record
ord-3679025e8ba34efb80248d9218ac6b26
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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