Reaction #1485

Reaction equation

3,4-dihydro-1-(2-thienyl)-4,4-dimethyl-6-acetylnaphthalene

4-carboxy benzaldehyde

NaOH

→

title compound

4-[3-oxo-3-(7,8-dihydro-5-(2-thienyl)-8,8-dimethyl-2-naphthalenyl)-1-propenyl]-benzoic acid

Solvents

MeOH

Conditions

Workup

1. 1
   Concentrationconcentrated under reduced pressure
2. 2
   workup.DISSOLUTIONthe residual oil dissolved in EtOAc
3. 3
   workup.ADDITIONThe solution was treated with 10% HCl
4. 4
   Washthe organic layer washed with H2O, and saturated aqueous NaCl
5. 5
   Otherbefore being dried over Na2 SO4
6. 6
   OtherRemoval of the solvents under reduced pressure

Procedure

To a solution of 62.6 mg (0.222 mmol) 3,4-dihydro-1-(2-thienyl)-4,4-dimethyl-6-acetylnaphthalene (Compound D33) in 4.0 mL of MeOH were added 33.4 mg (0.222 mmol) of 4-carboxy benzaldehyde, and 240.0 mg (6.00 mmol; 2.0 mL of 3M aqueous NaOH). The resulting solution was stirred at room temperature for 12 h, concentrated under reduced pressure, and the residual oil dissolved in EtOAc. The solution was treated with 10% HCl, and the organic layer washed with H2O, and saturated aqueous NaCl, before being dried over Na2 SO4. Removal of the solvents under reduced pressure gave the title compound as a pale green solid after recrystallization from EtOH.

Source