Ethyl 6-cyano-4,4-diphenyl-hex-2-enoate → Ethyl 6-cyano-4,4-diphenylhexanoate

HRID 1602162Notes

Reaction equation

HRID 1602162 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:2]>C(O)C.[Pd]>[C:1]([CH2:3][CH2:4][C:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:2]

Participants

4

Reactant 1

HCID 54399157Ethyl 6-cyano-4,4-diphenyl-hex-2-enoate

Product 1

HCID 19610260Ethyl 6-cyano-4,4-diphenylhexanoateYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography
  4. washeluting with (95:5) hexane/ethyl acetate

Sources & evidence

ORD record
ord-522560a42bc44a96beab3d300a26fd90
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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