Lithium Hydroxide → 2-(4-Methoxyphenyl)benzoxazole-4-carboxylic acid

HRID 969827Notes

Reaction equation

HRID 969827 reaction equation
[OH-].[Li+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:14](=[C:16]([C:20]([O:22]C)=[O:21])[CH:17]=[CH:18][CH:19]=3)[N:15]=2)=[CH:7][CH:6]=1>>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:14](=[C:16]([C:20]([OH:22])=[O:21])[CH:17]=[CH:18][CH:19]=3)[N:15]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 14616764Methyl 2-(4-methoxyphenyl)benzoxazole-4-carboxylate

Product 1

HCID 158135912-(4-Methoxyphenyl)benzoxazole-4-carboxylic acidYield 92%

Procedure

2-(4-Methoxyphenyl)benzoxazole-4-carboxylic acid was prepared via the lithium hydroxide mediated hydrolysis of methyl 2-(4-methoxyphenyl)benzoxazole-4-carboxylate as described in Step B of Example 14. This material was obtained in 92% yield as a white solid: δ 11.90 (br s, 1H), 8.25 (m, 2H), 8.13 (dd, J=7.8, 0.9 Hz, 1H), 7.79 (dd, J=7.8, 0.9 Hz, 1H), 7.48 (t, J=7.9 Hz, 1H), 7.08 (m, 2H), 3.93 (s, 3H); MS (ESI) m/z 270 [M+H]+

Workup

  1. customThis material was obtained in 92% yield as a white solid

Sources & evidence

ORD record
ord-c5869e6ce8db40cf83218f8f4d4eb6e1
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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