Sodium Hydroxide → 5-Cyclopropyl-3-phenyl-1,2-oxazole-4-carboxylic acid

HRID 2421157Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:8][O:9][C:10]=1[CH:11]1[CH2:13][CH2:12]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH:11]1([C:10]2[O:9][N:8]=[C:7]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:6]=2[C:4]([OH:5])=[O:3])[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-cyclopropyl-3-phenyl-isoxazole-4-carboxylic acid ethyl ester (408 mg, 1.58 mmol) in ethanol (4 mL) was added aqueous sodium hydroxide (1 N, 3.17 mL, 3.17 mmol) and the mixture was stirred for 3 h at 80° C. The ethanol was distilled off and the residue diluted with water (5 mL) and acified with aqueous HCl (IN) to pH=1. The resulting suspension was filtered off and washed with water affording the title compound (314 mg, 86%) as a white solid. MS: m/e=230.3[M+H]+.

Workup

distillationThe ethanol was distilled off
additionthe residue diluted with water (5 mL)
filtrationThe resulting suspension was filtered off
washwashed with water affording the title compound (314 mg, 86%) as a white solid

Sources & evidence

ORD record: ord-dafc731fe79e4bd88bcfd1b1d839dd6a
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956074B2

Reaction notes

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