Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(3-(trifluoromethoxy)phenyl)acrylate

HRID 520317Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 15 °C

Procedure

A mixture of 3-(trifluoromethoxy)benzaldehyde 158a (10.0 g, 52.6 mmol) and ethyl 2-(triphenylphosphoranylidene)acetate 158b (27.5 g, 78.9 mmol) in DCM (200 mL) was stirred at 15° C. for 2 h. See FIG. 4. The resulting mixture was concentrated under reduced pressure, and the crude was purified by column chromatography on silica gel (ethyl acetate:petroleum ether=1:8) to afford ethyl 3-(3-(trifluoromethoxy)phenyl)acrylate 158c (12.0 g, 88%) as yellow oil.

Workup

concentrationThe resulting mixture was concentrated under reduced pressure
customthe crude was purified by column chromatography on silica gel (ethyl acetate:petroleum ether=1:8)

Sources & evidence

ORD record: ord-72e8bb388ac3421bb528845f0aa0f1a7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326985B2

Reaction notes

Loading…