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

HRID 1377663Notes

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-d298f7c748ce4dabbf7cf05a27cd7d86
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665748

Reaction notes

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