Toluene → 4-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole

HRID 352072

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.ClCC(CCl)=O.[C:22]1([CH3:28])[CH:27]=CC=CC=1.O.O.O.[C:32]([O-:35])(=[O:34])[CH3:33].[Na+]>CO.CS(C)=O>[C:32]([O:35][CH2:28][C:22]1[N:13]=[C:11](/[CH:10]=[CH:9]/[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=2)[O:12][CH:27]=1)(=[O:34])[CH3:33]

Participants

Conditions

Temperature: 72.5 °C

Procedure

(E)-3-(4-(Trifluoromethyl)phenyl)-2-propenamide (10.0 g,46.5 mmol) and 1,3-dichloroacetone (11.0 g, 86.6 mmol) were added to toluene (50 ml), and the mixture was subjected to refluxing azeotropic dehydration using a Dean-Stark tube for 8.5 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added dimethyl sulfoxide (50 ml) and sodium acetate trihydrate (15.8 g, 116.1 mmol). The mixture was stirred at 70-75° C. for 4 hours. Methanol (50 ml) was added. After allowing-to cool to room temperature and stirring; the mixture was stirred under ice-cooling for 1 hour. The precipitated crystals were collected by filtration, washed with cold-methanol (30 ml) and dried under reduced pressure to give 4-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (13.1 g, yield 65%).

Workup

temperatureto refluxing azeotropic dehydration
customfor 8.5 hours
concentrationThe reaction mixture was concentrated under reduced pressure
temperatureAfter allowing-to cool to room temperature
stirringstirring
stirringthe mixture was stirred under ice-
temperaturecooling for 1 hour
filtrationThe precipitated crystals were collected by filtration
washwashed with cold-methanol (30 ml)
customdried under reduced pressure

Sources & evidence

ORD record: ord-6c7a09e552c3430f98ac75e781c5f0fa
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743924B2

Linked notes

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