Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]acrylate

HRID 1690607Notes

Reaction equation

HRID 1690607 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15].[CH2:16]([O:18][C:19]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:20])[CH3:17]>O1CCCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:21][C:19]([O:18][CH2:16][CH3:17])=[O:20])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 866332964-Hydroxy-3-(3-methoxypropoxy)benzaldehyde

Product 1

HCID 66907011Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]acrylateYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-hydroxy-3-(3-methoxypropoxy)benzaldehyde (15 g, 71.3 mmol) was dissolved in tetrahydrofuran (142 mL) and (ethoxycarbonylmethylene)triphenylphosphorane (24.8 g, 71.3 mmol) was added at room temperature portionwise. The mixture was then stirred overnight. The solvents were evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2) to yield 16 g (80%) of the desired product as a yellow oil of a mixture of E and Z isomers.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2)
  3. customto yield

Sources & evidence

ORD record
ord-b9bb2d5107014abca499a34c8e4b323a
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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