HCID 53674676, compound → HCID 19610239, compound

HRID 1602175Notes

Reaction equation

HRID 1602175 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)[CH2:6][CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])#[N:2]>CO.[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][CH2:8][C:9]([O:11][CH3:12])=[O:10])#[N:2]

Participants

4

Reactant 1

HCID 53674676HCID 53674676, compound

Product 1

HCID 19610239HCID 19610239, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 7-cyano-5,5-diphenyl-hept-2-enoate (1.4 1 g, 4.41 mmol) in MeOH (di00 mL) was added Pd/C (0.714 g). The reaction mixture was hydrogenated at 4 atm for 21 hr. 5 The catalyst was filtered and the filtrate was evaporated in vacuo. The oily residue (2 g) was purified by a silica gel column chromatography (eluting with 15:85 mixture of ethyl acetateihexane) to yield the desired product as a colorless oil (96 %): MS showed (M+H)+ e 322;H-NMR (CDCl3, δ): 1.25-1.36 (mn, 2H), 1.98-2.13 (m,. 4H), 2.26 (t, 2H, J =7.1 Hz). 2.49-2.58 (mn, 2H) 3 .65 (s, )H), 7.10-7.17 (mn, 4H), 7.21-7.36 (mn, 6H); IR (MIC) u 2951, 2247, 1735, 1444, 1196 cm-1 ; Anal. Calcd for C2 1H21N02 : C, 78.47; H, 7.2 1; N, 4.3 6; Found: C, 78.58; H, 7.12; N, 4.14.

Workup

  1. filtration5 The catalyst was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe oily residue (2 g) was purified by a silica gel column chromatography (eluting with 15:85 mixture of ethyl acetateihexane)

Sources & evidence

ORD record
ord-ae51539f1c5e4b63ba521faa726adbcb
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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