Reacción #1467

ord-b1bd58830652436484aeb0d21b29efe6

Ecuación de reacción

CCSC1=CCC(C)(C)c2ccc(Br)cc21
2-bromo-5,6-dihydro-5,5-dimethyl-8-(ethylthio)-naphthalene
C=Cc1ccc(C(=O)OCC)cc1
ethyl 4-vinylbenzoate
Cc1ccccc1P(c1ccccc1C)c1ccccc1C
tri-o-tolylphosphine
CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(SCC)=CCC3(C)C)cc1
title compound
CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(SCC)=CCC3(C)C)cc1
Ethyl (E)-4-[-2-(5,6-dihydro-5,5-dimethyl-8-(ethylthio)-naphthalen-2-yl)ethenyl]benzoate

Disolventes

Condiciones de reacción

Temperatura
90°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónThe reaction was concentrated in vacuo
  2. 2
    Otropurified by flash chromatography (silica, 2% ethyl acetate in hexane)

Procedimiento

To a degassed solution of 0.50 g (1.7 mmol) of 2-bromo-5,6-dihydro-5,5-dimethyl-8-(ethylthio)-naphthalene (Compound A36) and 0.45 g (2.5 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine, was added 109 mg (0.36 mmol) of tri-o-tolylphosphine and then 35 mg (0.16 mmol) of palladium(II) acetate. The reaction was heated at 90° C. for 2.25 h. The reaction was concentrated in vacuo and purified by flash chromatography (silica, 2% ethyl acetate in hexane) to afford the title compound as a colorless oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723666uspto-grants-1998_03