Hydrochloric Acid → HCID 59587532, compound

HRID 1410436Notes

Reaction equation

HRID 1410436 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-bcce3c18d1b8473ca1ba554c417f286b
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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