반응 #1492

반응 방정식

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

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas carefully added
2. 2
   기타to quench
3. 3
   기타the reaction
4. 4
   추출The product was extracted into Et2O
5. 5
   세척the combined organic layers washed with saturated aqueous NaCl
6. 6
   건조dried over MgSO4
7. 7
   기타Removal of the solvents under reduced pressure

실험 절차

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 product 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).

출처