Reaktion #1689344

Reaktionsgleichung

ethyl 6-cyano-4,4-diphenyl-hex-2-enoate

→

desired product

Ausbeute 87.8%

Ethyl 6-cyano-4.4-diphenyl-hexanoate

Ausbeute 87.8%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe catalyst was filtered
2. 2
   Einengenthe filtrate was concentrated in vacuo
3. 3
   SonstigeThe residue was purified by a silica gel column chromatography
4. 4
   Wascheneluting with (95:5) hexane/ethyl acetate

Vorschrift

A solution of ethyl 6-cyano-4,4-diphenyl-hex-2-enoate (22.06 g) in ethanol (500 mL) was hydrogenated in the presence of 10% Pd/C (2.2 g) under 4 atmospheric pressure for 17 hr. The catalyst was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography eluting with (95:5) hexane/ethyl acetate. The desired product (19.49 g) was obtained as colorless oil: MS showed (M+NH4)+ @ 339; 1H-NMR (CDCl3, δ): 1.20-1.25 (t, 3H), 1.95-2.06 (m, 4H), 2.38-2.52 (m, 4H), 4.03-4.12 (m, 2H), 7.10-7.36 (m, 1OH).

Quelle