2-Naphthalenecarboxaldehyde → 2-Propenoic acid, 3-(2-naphthalenyl)-, ethyl ester

HRID 743392Notes

Reaction equation

HRID 743392 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[CH2:13]([O:15][C:16]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17])[CH3:14]>C(#N)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:18][C:16]([O:15][CH2:13][CH3:14])=[O:17]

Participants

4

Reactant 2

HCID 62012-NaphthalenecarboxaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 44543982-Propenoic acid, 3-(2-naphthalenyl)-, ethyl esterYield 99.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3.00 g of 2-naphthaldehyde and 6.69 g of ethoxycarbonylmethylenetriphenylphosphorane in 100 ml of acetonitrile was heated under reflux for 1 hour, after which the reaction mixture was concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 4.32 g (yield 99%) of ethyl 3-(2-naphthyl)-2-propenoate as a colorless solid.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationafter which the reaction mixture was concentrated by evaporation under reduced pressure
  3. customThe resulting residue was purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-82b2db6a26aa451b876c9ae4b27fe949
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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