Reacción #52869

Ecuación de reacción

thiophenol

Et3N

methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate

methyl 5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate

Compound E2

methyl 5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate

H2O

→

title compound

Methyl-5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylate

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas carefully added
2. 2
   Otroto quench
3. 3
   Otrothe reaction
4. 4
   ExtracciónThe pruduct was extracted into Et2O
5. 5
   Lavadothe combined organic layers washed with saturated aqueous NaCl
6. 6
   Secadodried over MgSO4
7. 7
   OtroRemoval of the solvents under reduced pressure

Procedimiento

To a solution of methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate (Compound E2, 835.0 mg, 3.60 mmol) in 25.0 mL of THF at room temperature was added TiCl4 (670.0 mg, 3.55 mmol). Thereafter a solution of thiophenol (430.0 mg, 3.90 mmol) and Et3N (730.0 mg, 7.20 mmol) in 10 mL THF was added. The resulting brown mixture was stirred for 6 h before H2O was carefully added to quench the reaction. The pruduct was extracted into Et2O and the combined organic layers washed with saturated aqueous NaCl and dried over MgSO4. Removal of the solvents under reduced pressure afforded a solid from which the title compound was isolated as a yellow solid by column chromatography (5% EtOAc-hexanes).

Fuente