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

HRID 352074Notes

Reaction equation

C([O:4][CH2:5][C:6]1[N:7]=[C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[O:9][CH:10]=1)(=O)C.[OH-].[Na+].O>CS(C)=O>[OH:4][CH2:5][C:6]1[N:7]=[C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[O:9][CH:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

4-(Acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (20.0 g, 64.3 mmol) was dissolved in dimethyl sulfoxide (200 ml), and 2N-aqueous sodium hydroxide solution (35 mL 70.0 mmol) was added at 50° C. The mixture was stirred at about 40° C. for 15 min. Water (200 ml) was added at the same temperature. After allowing to cool to room temperature and stirring, the mixture was stirred at the same temperature for 1 hour. The precipitated crystals were collected by filtration, washed with water (60 ml) and dried under reduced pressure to give 4-(hydroxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (16.4 g, 61.1 mmol, yield 95%).

Workup

temperatureto cool to room temperature
stirringstirring
stirringthe mixture was stirred at the same temperature for 1 hour
filtrationThe precipitated crystals were collected by filtration
washwashed with water (60 ml)
customdried under reduced pressure

Sources & evidence

ORD record: ord-9a453d067a43415da755f74b9ea4e09a
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743924B2

Reaction notes

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