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

HRID 709676Notes

Reaction equation

HRID 709676 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])(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]=[C:11]([CH:12]=[CH:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 38487103-(Benzyloxy)-5-methoxybenzaldehyde

Product 1

HCID 91085057Ethyl 3-(3-(benzyloxy)-5-methoxyphenyl)acrylateYield 84.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-(benzyloxy)-5-methoxybenzaldehyde (5.50 g) in toluene (50 mL) was added ethyl (triphenylphosphoranylidene)acetate (7.90 g), and the mixture was heated under reflux for 4 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.00 g) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bb9d1d64b8e24e56918c731258c879df
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…