Reaction #1488

Reaction equation

methyl 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-2-naphthalenecarboxylate

Compound E5

methyl 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-2-naphthalenecarboxylate

NaOH

→

title compound

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

Solvents

EtOH

THF

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   Otherquenched with 1M HCl
3. 3
   ExtractionThe mixture was extracted with EtOAc
4. 4
   Washthe combined organic layers washed with H2O and saturated aqueous NaCl
5. 5
   Dryingbefore being dried over MgSO4
6. 6
   OtherRemoval of the solvents under reduced pressure

Procedure

To a solution of methyl 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-2-naphthalenecarboxylate (Compound E5, 430.0 mg, 1.44 mmol) in 3.0 mL of EtOH and 3.0 mL THF was added NaOH (240.0 mg, 6.00 mmol; 3.0 mL of a 2N aqueous solution). The resulting solution was warmed to 35° C. for 6 h, cooled to room temperature and quenched with 1M HCl. The mixture was extracted with EtOAc and the combined organic layers washed with H2O and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents under reduced pressure afforded the title compound as a pale yellow solid.

Source