Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(5-(benzyloxy)-2-methylphenyl)acrylate

HRID 709689Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:17])=[C:13]([CH:16]=1)[CH:14]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:17])=[C:13]([CH:14]=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-(benzyloxy)-2-methylbenzaldehyde (250 mg) in toluene (20 mL) was added ethyl (triphenylphosphoranylidene)acetate (379 mg), and the mixture was stirred at 60° C. for 15 hr. The reaction mixture was concentrated, diethyl ether was added, and the insoluble material was filtered off. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (200 mg) as a yellow oil.

Workup

concentrationThe reaction mixture was concentrated
additiondiethyl ether was added
filtrationthe insoluble material was filtered off
concentrationThe filtrate was concentrated
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c4fa1aea91e7475e9198735ac107cb04
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

Loading…