Hydrochloric Acid → Methyl 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate

HRID 1739044Notes

Reaction equation

Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[C:10]([F:28])[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C1CCN2C(=NCCC2)CC1.Cl>C1(C)C=CC=CC=1>[CH3:6][O:5][C:3](=[O:4])[CH:2]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])=[C:10]([F:28])[CH:9]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of methyl 2-bromo-3-[3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionate (14.2 g), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) (4.83 g) and toluene (150 ml) was stirred at 80 to 90° C. for 2 hours, and then poured into 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give methyl3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)-cinnamate (10.0 g, 86%). This product was recrystallized from dichloromethane-methanol. Colorless prisms, mp: 167-168° C.

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-517f058724e54185a5c961abad8528ab
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05965589

Reaction notes

Loading…