Hydrochloric Acid → HCID 59587532, compound

HRID 714937Notes

Reaction equation

HRID 714937 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][C:11]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=1.[OH-].[K+].Cl>CO>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[O:10][C:11]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59587634HCID 59587634, compound

Product 1

HCID 59587532HCID 59587532, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of ethyl 2-(2,6-difluorophenyl)-5-(thiophen-2-yl)oxazole-4-carboxylate (0.096 g, 0.29 mmol) in MeOH (6 mL) was added 1M potassium hydroxide solution (8 mL, 8.0 mmol) and the resulting mixture stirred at 55° C. overnight. The reaction was cooled to room temperature, acidified with 4N HCl and extracted with DCM. The combined organic phase was dried over MgSO4 and the solvent removed in vacuo to afford 2-(2,6-difluorophenyl)-5-(thiophen-2-yl)oxazole-4-carboxylic acid (0.078 g, 0.25 mmol, 89%) as an off white solid which was used without further purification. LCMS (1) Rt: 1.41 min; m/z (ES+) 308.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with DCM
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-861102ba4d8e49579d65f5cac65a7cfd
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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