Reaktion #2328213

Reaktionsgleichung

HCl

( 12 )

Ethyl 4-({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene) methyl]phenyl}oxy)butanoate

NaOH

→

title compound 13

Ausbeute 84.1%

4-({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy) butanoic acid

Ausbeute 84.1%

Lösungsmittel

THF EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe hydrolysis procedure
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   SonstigeStandard work-up followed by purification

Vorschrift

The hydrolysis procedure described for 11 (example 5, step 3) was used. A solution of ethyl 4-({4-[(4-fluorophenyl) (3,3,5,5-tetramethylcyclohexylidene) methyl]phenyl}oxy) butanoate) (12) (0.665 g, 1.47 mmol) in THF/EtOH (1:1, 10 mL) was treated with 1 N NaOH (5 mL, excess) at 70° C. for 1 h. The reaction mixture was cooled and poured into 20% aqueous HCl (40 mL). Standard work-up followed by purification afforded 0.525 g (84%) of the title compound 13 as a white foam. 1H NMR (300 MHz, DMSO-d6): δ12.13 (br s, 1H), 7.15 (d, J=6.6 Hz, 2H), 7.12 (d, J=9.6 Hz, 2H), 7.06 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.4 Hz, 2H), 3.94 (t, J=6.3 Hz, 2H), 2.37 (t, J=7.2 Hz, 2H), 1.93 (s, J=2H), 1.89 (s, 2H), 1.76 (quintet, J=6.3 Hz, 2H), 1.27 (s, 2H), 0.89 (s, 12H). LCMS (ESI): m/z 423 (M−H)−. Anal. Calcd for C27H33FO3, C, 76.39, H, 7.83, F, 4.47. Found: C, 76.30, H, 7.90, F, 4.52.

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