Reaktion #1156415

Reaktionsgleichung

acetic acid 2-cyclopentyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester

potassium hydroxide

→

title compound

Ausbeute 100.0%

2-Cyclopentyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol

Ausbeute 100.0%

Lösungsmittel

tetrahydrofuran

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter 1.5 h the reaction mixture was concentrated under reduced pressure
2. 2
   ExtraktionThe solution was extracted with diethyl ether (300 mL)
3. 3
   Waschenthe diethyl ether layer was washed twice with water
4. 4
   Trocknendried (Na2SO4)
5. 5
   EinengenConcentration under reduced pressure

Vorschrift

To acetic acid 2-cyclopentyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester (2.7 g, 5.4 mmol) in tetrahydrofuran (88 mL) and methanol (30 mL) at room temperature was added dropwise an aqueous potassium hydroxide (6.5 mL of a 1N solution, 6.5 mmol). After 1.5 h the reaction mixture was concentrated under reduced pressure. The resulting residue was combined with water (200 mL) and acidified with 10% aqueous hydrochloric acid to a pH of 1. The solution was extracted with diethyl ether (300 mL) and the diethyl ether layer was washed twice with water and dried (Na2SO4). Concentration under reduced pressure gave the title compound as a white solid (2.4 g, 100%): (DMSO-d6): δ9.54 (s, 1H), 8.16 (d, 1H), 7.61 (m, 1H), 7.52 (s, 1H), 7.43 (m, 1H), 7.03 (s, 1H), 6.93 (m, 2H), 3.32 (m, 1H), 2.41 (s, 3H), 1.94 (m, 2H), 1.58 (s, 3H), 1.72-1.42 (m, 6H); MS(EI): [M+], 1 bromine isotope pattern, 450/452; Anal. Calc. for C25H23BrOS: C, 66.52; H, 5.13; N, 0.00. Found: C, 67.17; H, 5.25; N, 0.04.

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