Reaktion #411410

Reaktionsgleichung

ethyl (E)4-[2-(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)- 2-naphthalenyl)ethenyl)-benzoate

Compound 44

ethyl (E)4-[2-(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)- 2-naphthalenyl)ethenyl)-benzoate

LiOH

MeOH

→

title compound

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in H2O
4. 4
   Extraktionextracted with hexanes
5. 5
   Extraktionextracted with Et2O
6. 6
   WaschenThe combined organic layers were washed with saturated aqueous NaCl
7. 7
   workup.ADDITIONdiluted with EtOAc
8. 8
   Sonstigeto give a clear solution
9. 9
   Trocknendried over Na2SO4
10. 10
    SonstigeThe solvents were removed under reduced pressure

Vorschrift

To a solution of 65.0 mg (0.190 mmol) of ethyl (E)4-[2-(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)- 2-naphthalenyl)ethenyl)-benzoate (Compound 44) in 4.0 ml of THF was added 30.0 mg of LiOH (0.909 mmol, 1.0 ml of a 1.1M solution) and 1.0 ml of MeOH. The solution was heated to 55° C. for 3 hours, cooled to room temperature, and concentrated under reduced pressure. The residue was dissolved in H2O and extracted with hexanes. The aqueous layer was acidified to pH 1 with 10% HCl, and extracted with Et2O. The combined organic layers were washed with saturated aqueous NaCl, diluted with EtOAc to give a clear solution, and dried over Na2SO4. The solvents were removed under reduced pressure to give the title compound as a colorless solid. 1H NMR (d6-DMSO): δ 7.86 (2H, d, J=8.4 Hz), 7.66 (2H, d, J=8.4 Hz), 7.58 (1H, dd, J=1.7, 8.1 Hz), 7.41 (1H, d, J=8.1 Hz), 7.28 (1H, d, J=16.5 Hz), 7.23 (4H, s), 7.08 (1H, d, J=1.7 Hz), 7.07 (1H, d, J=16.5 Hz), 5.97 (1H, t, J=4.6 Hz), 2.35 (3H, s), 2.31 (2H, d, J=4.6 Hz), 1.29 (6H, s).

Quelle