Reaktion #705236

Reaktionsgleichung

ethyl

ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(3,5-dimethylphenyl)-2-naphthalenyl)ethynyl]-benzoate

[(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl]amino]-benzoate

Compound 42

Ethyl 4[[(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl)thiocarbonyl]amino]-benzoate

NaOH

→

title compound

4-[[(5,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl)thiocarbonyl]amino]-benzoic acid

Lösungsmittel

EtOH

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched by the addition of 10% HCl
2. 2
   ExtraktionExtraction with EtOAc
3. 3
   Trocknendrying of the organic layers over MgSO4
4. 4
   Sonstigeprovided a solid
5. 5
   Sonstigeafter removal of the solvent under reduced pressure
6. 6
   SonstigeCrystallization from CH3CN

Vorschrift

To a solution of 84.0 mg (0.184 mmol) ethyl 4[[(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl]amino]-benzoate (Compound 42) in 2.0 ml EtOH and 2.0 ml of THF was added 60.0 mg NaOH (1.50 mmol, 1.5 ml of a 1M aqueous solution). After stirring at room temperature overnight, the reaction was quenched by the addition of 10% HCl. Extraction with EtOAc, and drying of the organic layers over MgSO4, provided a solid after removal of the solvent under reduced pressure. Crystallization from CH3CN afforded the title compound as a yellow solid. 1H NMR (d6-acetone): δ 10.96 (1H, s), 8.05 (4H, m), 7.72 (1H, dd, J=2.0, 8.0 Hz), 7.54 (1H, s), 7.46 (1H, d, J=8.1 Hz), 7.20 (4H, m), 6.04 (1H, t, J=4.7 Hz), 2.38 (2H, d, J=4.7 Hz), 2.33 (3H, s), 1.35 (6H, s).

Quelle