Hydrochloric Acid → 3-Phenyl-5-(2-phenylethyl)isoxazole-4-carboxylic acid

HRID 840130

Reaction equation

[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=[O:14].[Li].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>O1CCCC1.CCCCCC.O>[C:7]1([C:4]2[C:3]([C:13]([OH:15])=[O:14])=[C:2]([CH2:1][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:6][N:5]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1.5 g of 5-methyl-3-phenyl-4-isoxazolecarboxylic acid in 50 mL of anhydrous tetrahydrofuran stirred at −78 ° C. under N2 atmosphere, 5.9 mL of a 2.5M solution of n-buthyl lithium in n-hexane was added and the solution was stirred at −78° C. for 2 hours. Afterwards, 0.89 mL of benzyl bromide was added at −78° C. and the solution stirred at room temperature for 2 hours. After overnight resting, the solution was poured into water (300 mL), acidified with hydrochloric acid and extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water, dried (sodium sulphate) and the solvents were evaporated to dryness. The solid residue was washed with petroleum ether to give 1.82 g (84%) of the title compound as an amorphous solid.

Workup

stirringthe solution stirred at room temperature for 2 hours
waitAfter overnight resting
extractionextracted with ethyl acetate (2×200 mL)
washThe combined organic layers were washed with water
dry with materialdried (sodium sulphate)
customthe solvents were evaporated to dryness
washThe solid residue was washed with petroleum ether

Sources & evidence

ORD record: ord-24fd1e98a5f84dc5aa4538b128321716
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365591B1

Linked notes

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