3-Hydroxybenzaldehyde → 3-[(4,5-Diphenyl-2-oxazolyl)methoxy]benzaldehyde

HRID 257642Notes

Reaction equation

HRID 257642 reaction equation
Br[CH2:2][C:3]1[O:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.[I-]>[C:8]1([C:6]2[N:7]=[C:3]([CH2:2][O:20][C:21]3[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=3)[CH:24]=[O:25])[O:4][C:5]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5685992-Bromomethyl-4,5-diphenyl-oxazole

Product 1

HCID 117257323-[(4,5-Diphenyl-2-oxazolyl)methoxy]benzaldehydeYield 78.3%

Reagents, catalysts & solvents 2

HCID 30165Iodide IonCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-bromomethyl-4,5-diphenyloxazole (26.72 g, 85 mmol) obtained according to D. L. Aldous, et al., J. Org. Chem. 2, 228-334 (1937), 3-hydroxybenzaldehyde (9.34 g, 76 mmol), potassium carbonate (12.92 g, 93 mmol), potasssium iodide (0.5 g) and dimethylformamide (250 mL) was stirred at 110° C. After 45 minutes, the mixture was cooled, diluted with water and extracted with diethyl ether (3×). The combined extracts were washed with water (3×), dried over sodium sulfate and concentrated in vacuo to give an oil which was chromatographed on a column of silica gel. Elution with a mixture of hexanes and diethyl ether (2:1) afforded 3-[(4,5-diphenyl-2-oxazolyl)methoxy]benzaldehyde (21.16 g, 70%). An analytical sample was recrystallized from a mixture of CH2Cl2 and hexanes and had mp 72°-75° C.

Workup

  1. customobtained
  2. temperaturethe mixture was cooled
  3. extractionextracted with diethyl ether (3×)
  4. washThe combined extracts were washed with water (3×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. customwas chromatographed on a column of silica gel
  9. washElution
  10. additionwith a mixture of hexanes and diethyl ether (2:1)

Sources & evidence

ORD record
ord-d17f18c770564243aca9181ee475a73b
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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