Ethyl 2-(2,2,2-trifluoroethyl)thiazole-4-carboxylate → 2-(2,2,2-Trifluoroethyl)-1,3-thiazole-4-carboxylic acid

HRID 471142Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9]([O:11]CC)=[O:10])[N:8]=1>Cl.O>[F:15][C:2]([F:1])([F:14])[CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9]([OH:11])=[O:10])[N:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ethyl 2-(2,2,2-trifluoroethyl)thiazole-4-carboxylate (example 67, step c) (0.3 g) in concentrated hydrochloric acid (7 mL) and water (7 mL) was heated at 80° C. for 5 hours under nitrogen. The solvent was evaporated under a stream of nitrogen and the residue partitioned between ethyl acetate (40 mL) and brine (3 mL). The organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.23 g.

Workup

customThe solvent was evaporated under a stream of nitrogen
customthe residue partitioned between ethyl acetate (40 mL) and brine (3 mL)
dry with materialThe organic layer was dried over sodium sulphate
filtrationfiltered
customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record: ord-3ad11f1093ed4264bb13410edb2826a8
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629271B2

Reaction notes

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