Chloroacetone → HCID 69225664, compound

HRID 2113912Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=[O:21])[O:14][N:13]=2)=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:33][C:34](=[O:36])[CH3:35]>>[O:36]=[C:34]([CH3:35])[CH2:33][O:21][C:20](=[O:22])[C:19]1[CH:23]=[CH:24][CH:25]=[C:17]([C:15]2[O:14][N:13]=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:11][CH:10]=3)[CH:16]=2)[CH:18]=1

Participants

Reactant 3

HCID 6571Chloroacetone

HCID 11430Potassium Carbonate

HCID 692218573-{3-[4-(2-Methoxyethoxy)phenyl]-1,2-oxazol-5-yl}benzoic acid

Product 1

HCID 69225664HCID 69225664, compound

Conditions

Temperature: 55 °C

Procedure

In a 25 ml round flask, 150 mg (0.44 mmol) of 3-{3-[4-(2-methoxy-ethoxy)-phenyl]-isoxazol-5-yl}-benzoic acid are dissolved. Then, 122 mg (0.88 mmol, 4 eq.) of K2CO3 and 49 mg (0.53 mmol, 1.2 eq.) of 1-chloro-propan-2-one are added and the suspension heated to 55° C. under nitrogen. After 48 h, the reaction is cooled to room temperature and the solvent evaporated. Chromatographic purification (10 g SiO2; eluent: hexane/ethyl acetate 1:0 to 4:6) yields the title compound as a white solid. Mass spectrum: m/z (M+H)+: 396.0

Workup

temperaturethe reaction is cooled to room temperature
customthe solvent evaporated
customChromatographic purification (10 g SiO2; eluent: hexane/ethyl acetate 1:0 to 4:6)

Sources & evidence

ORD record: ord-8c07859afe5a4f7d8f28d42bc2d807fe
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432293B2

Reaction notes

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