Reaction #568408

Reaction equation

Et2O

5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid

Compound E6

5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid

2-trimethylsilylethyl 4-hydroxybenzoate

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

title compound

2-Trimethylsilylethyl-4-[[(5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoate

Solvents

DMF

Conditions

Workup

1. 1
   Washthe solution washed with H2O, 5% HCl, saturated aqueous NaCO3, and saturated aqueous NaCl
2. 2
   Dryingbefore being dried over MgSO4
3. 3
   OtherRemoval of the sovents under reduced pressure and column chromatography (10% EtOAc-hexanes) of the residual oil

Procedure

A solution of 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid (Compound E6, 79.0 mg, 0.280 mmol), 2-trimethylsilylethyl 4-hydroxybenzoate (73.3 mg, 0.308 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (70.0 mg, 0.364 mmol), and 4-N,N-dimethylaminopyridine (44.5 mg, 0.364 mmol) in 2.0 mL DMF was stirred overnight at room temperature. Et2O (100 mL) was added and the solution washed with H2O, 5% HCl, saturated aqueous NaCO3, and saturated aqueous NaCl before being dried over MgSO4. Removal of the sovents under reduced pressure and column chromatography (10% EtOAc-hexanes) of the residual oil afforded the title compound as a colorless solid.

Source