Réaction #52869

Équation de réaction

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

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas carefully added
2. 2
   Autreto quench
3. 3
   Autrethe reaction
4. 4
   ExtractionThe pruduct was extracted into Et2O
5. 5
   Lavagethe combined organic layers washed with saturated aqueous NaCl
6. 6
   Séchagedried over MgSO4
7. 7
   AutreRemoval of the solvents under reduced pressure

Mode opératoire

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).

Source