Pyridine → Methyl 2-chloro-4-(4-trifluoromethylphenyl)-5-oxazolepropionate

HRID 395643Notes

Reaction equation

O=[C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[C:4]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[O:3]1.P(Cl)(Cl)([Cl:25])=O.N1C=CC=CC=1>O>[Cl:25][C:2]1[O:3][C:4]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[N:6]=1

Participants

Conditions

Temperature: 102.5 °C

Procedure

A mixture of methyl 3-[2-oxo-4-(4-trifluoromethylphenyl)-4-oxazolin-5-yl]propionate (3.90 g), phosphorus oxychloride (11.5 g) and pyridine (0.98 g) was heated to 100-105° C. and stirred for 1 hour. The reaction mixture was added dropwise to heated water (100 ml) of 30 ° C. and extracted with ethyl acetate (150 ml×2). The organic layer was washed with a saturated aqueous solution of sodium chloride (100 ml), and dried over anhydrous magnesium sulfate. The organic layer was concentrated, the residue was subjected to silica gel column chromatography, and methyl 2-chloro-4-(4-trifluoromethylphenyl)-5-oxazolepropionate was obtained as a yellow oil (2.66 g, 64%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

Workup

additionThe reaction mixture was added dropwise
extractionextracted with ethyl acetate (150 ml×2)
washThe organic layer was washed with a saturated aqueous solution of sodium chloride (100 ml)
dry with materialdried over anhydrous magnesium sulfate
concentrationThe organic layer was concentrated

Sources & evidence

ORD record: ord-e3009b0d9c7e4ff18123de1f2eb2867e
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605629B1

Reaction notes

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