Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(2-methoxy-5-(methoxycarbonyloxy)phenyl)acrylate

HRID 709694Notes

Reaction equation

[C:1](=[O:15])([O:13][CH3:14])[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([CH:11]=O)[CH:4]=1.C1(P(=[CH:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][C:1]([O:13][CH3:14])=[O:15])=[CH:4][C:5]=1[CH:11]=[CH:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-formyl-4-methoxyphenyl methyl carbonate (10.0 g) in toluene (10 mL) was added ethyl (triphenylphosphoranylidene)acetate (21.5 g), and the mixture was stirred at 80° C. for 15 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (12.0 g) as a yellow oil.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-ee21f1c7d4da42208205e940a2a6d0de
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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