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

HRID 415644Notes

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-4e6f58dfdbb14c099a1365cfb18d06ec
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088791B2

Reaction notes

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