Hydrochloric Acid → 5-(4-Methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxylic acid

HRID 389726Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 5-(4-methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxylate in MeOH (2 mL) and DCM (0.5 mL) was added 1M aqueous lithium hydroxide solution (2 mL, 2 mmol). The reaction mixture was stirred at 50° C. overnight and then 2M aqueous HCl (0.125 mL) was added and the solvent removed in vacuo to afford 5-(4-methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxylic acid which was used without further purification. LCMS (1) Rt: 1.34 min; m/z (ES+) 302.

Workup

customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-c76433dea62c42c2bc7f74ee5e54d621
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378095B2

Reaction notes

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