Reaktion #510065

Reaktionsgleichung

22

(E)-10a-(4-(Benzyloxy)phenyl)-1-fluoro-8,9,10,10a-tetrahydro-7H-benzo[b]-cyclohepta[d]furan

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title product

Ausbeute 69.6%

(E)-4-(1-Fluoro-8,9,10,10a-tetrahydro-7H-benzo[b]cyclohepta-[d]furan-10a-yl)phenol

Ausbeute 69.6%

Lösungsmittel

ethyl acetate

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA balloon filled with H2
2. 2
   Sonstigewas fitted
3. 3
   SonstigeH2 was bubbled through the solution for 15 s
4. 4
   FiltrationThe mixture was filtered after 15 min

Vorschrift

10% Palladium on activated carbon (few mg) was added to a solution of 22 (15 mg) in ethyl acetate (2 mL) and ethanol (2 mL). A balloon filled with H2 was fitted and H2 was bubbled through the solution for 15 s. The mixture was filtered after 15 min, TLC indicated 50% conversion of 22. Work-up by flash chromatography (eluent: dichloromethane −>5% ethyl acetate in dichloromethane) afforded 8 mg of the title product. Starting material (5 mg) was recovered. LC-MS confirmed m/z=295 (M−1). 1H-NMR (400 MHz, CDCl3): δ ppm 7.49-7.46 (m, 2H), 7.05-7.00 (m, 1H), 6.81-6.79 (m, 2H), 6.61-6.59 (m, 1H), 6.53-6.48 (m, 1H), 5.73 (dd, J=4.8, 9.2 Hz, 1H), 3.07-3.02 (m, 1H), 2.00-1.20 (m, 8H).

Quelle