Reaction #1334

Reaction equation

4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid

4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl) ethynyl]benzoic acid

Compound 7

4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl) ethynyl]benzoic acid

dimethylaminopyridine

trimethylsilylethanol

1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride

→

Trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate

title compound

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Washwashed with sat. aqueous NaHCO3 and brine
2. 2
   Dryingdried over Na2SO4
3. 3
   Concentrationconcentrated in vacuo to an oil
4. 4
   OtherPurification by flash chromatography (silica, 10% EtOAc-hexane)

Procedure

To a solution of 0.24 g (0.73 mmol) of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid (Compound 7) in 10 ml of dry CH2Cl2 was added 0.09 g (0.74 mmol) of dimethylaminopyridine, 0.115 ml (0.80 mmol) of trimethylsilylethanol and 0.17 g (0.88 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. The reaction mixture was stirred at 25° C. for 5 hours, washed with sat. aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to an oil. Purification by flash chromatography (silica, 10% EtOAc-hexane) yielded the title compound as a white solid.

Source