Reaktion #2328215

Reaktionsgleichung

HCl

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

LiAlH4

→

title compound ( 15 )

Ausbeute 80.2%

2-({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)ethanol

Ausbeute 80.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with EtOAc (10 mL)
2. 2
   Sonstigestirring for an additional 10 min
3. 3
   SonstigeReaction mixture
4. 4
   Extraktionextracted with EtOAc (4×30 mL)
5. 5
   WaschenThe combined organic layer was washed with brine (1×30 mL)
6. 6
   Trocknendried (Na2SO4)
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   Sonstigeto afford the crude product
9. 9
   SonstigeThe product was purified by silica gel column chromatography

Vorschrift

To a solution of ethyl({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)acetate 10 (0.580 g, 1.336 mmol) in anhydrous THF (25 mL) was added LiAlH4 (3.4 mL, 3.42 mmol, 1.0 M solution in THF) drop-wise under N2 atmosphere at room temperature. The resultant solution was stirred at RT for 0.5 h. The reaction mixture was quenched with EtOAc (10 mL) and continued the stirring for an additional 10 min. Reaction mixture was poured into 15% aqueous HCl (50 mL) and then extracted with EtOAc (4×30 mL). The combined organic layer was washed with brine (1×30 mL), dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by silica gel column chromatography using hexanes: EtOAc (19:1 to 4:1) as an eluent to afford 0.41 g (79%) of the title compound (15) as white foam. 1H NMR (400 MHz, DMSO-d6): δ 7.16-7.06 (m, 4H), 7.03 (d, J=8.4 Hz, 2H), 6.84 (d, J=6.4 Hz, 2H), 4.83 (t, J=5.6 Hz, 1H), 3.92 (t, J=5.2 Hz, 2H), 3.67 (q, J1=10.8 Hz, J2=5.2 Hz, 2H), 1.90 (s, 2H), 1.86 (s, 2H), 1.24 (s, 2H), 0.87 (s, 6H), 0.87 (6H). LCMS (APCI): m/z 405 (M+Na)+.

Quelle