Vanillin → 3-Methoxy-4-[2-(5-methyl2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

HRID 479187Notes

Reaction equation

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

Participants

Reactant 2

HCID 1183Vanillin

HCID 105407732-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate

Product 1

HCID 180035853-Methoxy-4-[2-(5-methyl2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

Procedure

In analogy to the procedures described in examples 114 b], c] and d], vanilline was reacted with methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester [PCT Int. Appl. (2000) WO0008002] to give 3-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde. Treatment of 3-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde with (benzyloxycarbonyl-methoxy-methyl)-triphenyl-phosphonium chloride then gave 2(Z,E)-methoxy-3-{3-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-acrylic acid benzyl ester, which was hydrogenated to yield [rac]-2-methoxy-3-{3-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid as colorless solid.

Sources & evidence

ORD record: ord-354d502d28274b37bc6f90f5d8c7f460
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642389B2

Reaction notes

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