4-Hydroxybenzaldehyde → 4-(2-Phenyl-4-oxazolylmethoxy)benzaldehyde

HRID 1720036Notes

Reaction equation

HRID 1720036 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.CS(C)=O.ClC[C:16]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:20][CH:19]=[CH:18][O:17]1.[C:27](=O)([O-])[O-].[Cs+].[Cs+]>O>[C:21]1([C:16]2[O:17][CH:18]=[C:19]([CH2:27][O:1][C:2]3[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=3)[N:20]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 224199112-(Chloromethyl)-2-phenyloxazole

Product 1

HCID 108265134-(2-Phenyl-4-oxazolylmethoxy)benzaldehydeYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (1.9 g, 17.0 mmol), dimethyl sulfoxide (50 mL), 2-(chloromethyl)-2-phenyloxazole (3.3 g, 17.0 mmol) and cesium carbonate (11.0 g, 34.0 mmol) was stirred at room temperature for 16 hours. The mixture was poured into water (400 mL) and filtration of the resultant precipitate afforded the crude product. Crystallization of the solids from ethyl acetate gave the product as a light yellow solid in 90.5 % yield, m.p. 94°-96° C. MS (EI, m/e): 279 (M)+

Workup

  1. customafforded the crude product
  2. customCrystallization of the solids from ethyl acetate

Sources & evidence

ORD record
ord-7cd0b684c47d4a6696a0a569fe29c037
Source dataset
uspto-grants-1996_04
Patent number
US05504097

Reaction notes

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