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

HRID 1289327Notes

Reaction equation

HRID 1289327 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.O>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

7

Reactant 4

HCID 962WaterHCID 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 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).

Workup

  1. additionwas carefully added
  2. customto quench
  3. customthe reaction
  4. extractionThe pruduct 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-0be95b7ca7684d00855e4268599e63a3
Source dataset
uspto-grants-1998_05
Patent number
US05747542

Reaction notes

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