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

HRID 1699331Notes

Reaction equation

HRID 1699331 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8](=O)[C:7]=2[CH:6]=1)=[O:4].[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>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:11]([CH3:16])([CH3:15])[CH2:10][CH:9]=[C:8]([S:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:7]=2[CH:6]=1)=[O:4]

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-1754fb198d5a4baf905b7ee4ed5c37f4
Source dataset
uspto-grants-2002_02
Patent number
US06344561B2

Reaction notes

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