3-Hydroxybenzaldehyde → 3-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde

HRID 1857534Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-chloromethyl-5-methyl-2-phenyloxazole (20.8 g), 3-hydroxybenzaldehyde (12.2 g), potassium carbonate (27.6 g) and N,N-dimethylformamide (DMF) (200 ml) was heated at 90° C. for 2 hours. The reaction mixture was poured into water, and subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate (MgSO4). The solvent was distilled off, whereby 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde (26.5 g, 90%) was obtained. Recrystallization from ethanol gave colorless prisms. Melting point: 67-68° C.

Workup

extractionsubjected to extraction with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried over magnesium sulfate (MgSO4)
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-51b65b28e8a746ef8a4df277f8592388
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147099

Reaction notes

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