Hydrochloric Acid → 2-(2,6-Difluorophenyl)-5-ethoxyoxazole-4-carboxylic acid

HRID 714976Notes

Reaction equation

HRID 714976 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]([O:19][CH2:20][CH3:21])=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=1.Cl>[OH-].[K+]>[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]([O:19][CH2:20][CH3:21])=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59587626Ethyl 2-(2,6-difluorophenyl)-5-ethoxyoxazole-4-carboxylate

Product 1

HCID 595875182-(2,6-Difluorophenyl)-5-ethoxyoxazole-4-carboxylic acidYield 67.6%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of ethyl 2-(2,6-difluorophenyl)-5-ethoxyoxazole-4-carboxylate (2.10 g, 7.1 mmol) in 1M aqueous potassium hydroxide and heated to 100° C. for 6 hours. The mixture was then cooled to 0° C. and acidified to pH 3 by 2M aqueous HCl. The resulting white solid was filtered, washed with water and dried in a vacuum oven to afford 2-(2,6-difluorophenyl)-5-ethoxyoxazole-4-carboxylic acid (1.28 g, 4.8 mmol, 67%). 1H NMR (CD3OD) δ 1.52 (3H, t), 4.61 (2H, q), 7.19 (2H, t), 7.61 (1H, m). LCMS (1) Rt: 1.09 min; m/z (ES+) 270.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. filtrationThe resulting white solid was filtered
  3. washwashed with water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-562db4d727fb474281e69dbccfeb28fb
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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