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

HRID 2394205Notes

Reaction equation

HRID 2394205 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9](=O)[C:8]2[CH:7]=[C:6]([C:13]([O:15][CH3:16])=[O:14])[CH:5]=[CH:4][C:3]1=2.[C:18]1([SH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(CC)CC>C1COCC1.Cl[Ti](Cl)(Cl)Cl>[CH3:16][O:15][C:13]([C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:17])([CH3:1])[CH2:11][CH:10]=[C:9]([S:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8]=2[CH:7]=1)=[O:14]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 10681077Methyl 5,5-dimethyl-5,6 dihydro-naphthalen-8(7h)-one-2-carboxylate2×

Product 1

HCID 22571588Methyl 5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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 H2 0 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).

Workup

  1. additionwas carefully added
  2. customto quench
  3. customthe reaction
  4. extractionThe product was extracted into Et2O
  5. washthe combined organic layers washed with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. customRemoval of the solvents under reduced pressure

Sources & evidence

ORD record
ord-ad78e81f122343d98803052dcc67e091
Source dataset
uspto-grants-1998_09
Patent number
US05808124

Reaction notes

Loading…