Hydrochloric Acid → 3-[4-(5-Methoxycarbonyl-1-pentenyl)phenyl]isoxazole-4-carboxylic acid

HRID 2111026Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.[C:16]([O:23][CH3:24])(=[O:22])[CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>O1CCOCC1.C(N(CC)C(C)C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][O:23][C:16]([CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1)=[O:22]

Participants

Conditions

Temperature: 100 °C

Procedure

3-(4-Iodophenyl)isoxazole-4-carboxylic acid (315 mg, 1.0 mmol) was dissolved in a mixed solvent of 1,4-dioxane (5 ml) and diethylisopropylamine (2.5 ml), methyl 5-hexenoate (179 mg, 1.4 mmol), tri-(o-tolyl)phosphine (122 mg, 0.4 mmol) and palladium acetate (22.4 mg, 0.1 mmol) were added, and the mixture was stirred overnight at 100° C. 1N Hydrochloric acid was added, and the mixture was extracted once with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=7:3-6:4) to give the title compound (250 mg, 79%).

Workup

additionwere added
extractionthe mixture was extracted once with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=7:3-6:4)

Sources & evidence

ORD record: ord-c9e8ac7102724a18ab02e2e4362b260d
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517996B2

Reaction notes

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