Triethylamine → 4-Tert-butyl 3-ethyl 5-(3-iodophenyl)isoxazole-3,4-dicarboxylate

HRID 1375685Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[CH3:25][CH2:26][O:27][C:28](/[C:30](/Cl)=[N:31]\O)=[O:29]>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([C:8]2[O:17][N:31]=[C:30]([C:28]([O:27][CH2:26][CH3:25])=[O:29])[C:9]=2[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 3-(3-iodophenyl)-3-oxopropanoate (1.91 g, 5.52 mmol) was dissolved in ethanol (6 mL), cooled to 0° C., and Et3N (558 mg, 5.52 mmol) was added. After stirring 20 minutes, ethyl chlorooximidoacetate (836 mg, 5.52 mmol) in EtOH (3 mL) was added to the reaction mixture over 30 min. The reaction mixture was warmed to ambient temperature and stirred overnight. The mixture was concentrated in vacuo and purified by column chromatography (0–13% ethyl acetate in hexanes) to provide the titled compound (860 mg, 35%).

Workup

temperatureThe reaction mixture was warmed to ambient temperature
stirringstirred overnight
concentrationThe mixture was concentrated in vacuo
custompurified by column chromatography (0–13% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-c22ad55f1beb4683a358d43599c40d90
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169797B2

Reaction notes

Loading…