3-Chloro-2-butanone → 2-(4-Methoxy-phenyl)-4,5-dimethyl-oxazole

HRID 538569Notes

Reaction equation

Cl[CH:2]([CH3:6])[C:3](=O)[CH3:4].[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=1>>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]2[O:14][C:2]([CH3:6])=[C:3]([CH3:4])[N:15]=2)=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 200263-Chloro-2-butanone

HCID 769594-Methoxybenzamide

Product 1

HCID 189829612-(4-Methoxy-phenyl)-4,5-dimethyl-oxazoleYield 83.6%

Conditions

Temperature: 115 °C

Procedure

A mixture of 3-Chloro-2-butanone (2.1 g, 10.0 mmol) and 4-methoxybenzamide (0.30 g, 1.0 mmol) was heated at 115° C. for 15 h under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure and the residue was purified over silica gel (230-400 M, 20% EtOAc-Hexane) to get the desired product (0.17 g, 42%) as a white solid. The corresponding chloro derivative was also prepared by the same general method.

Workup

customAfter the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure
customthe residue was purified over silica gel (230-400 M, 20% EtOAc-Hexane)

Sources & evidence

ORD record: ord-2fc9b50ee16d406287a89371fd62a344
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865736B2

Reaction notes

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