Dimethyl 3-(cyanomethylidene)pentanedioate → Dimethyl 3-(cyanomethyl)pentanedioate

HRID 552324Notes

Reaction equation

HRID 552324 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5](=[CH:11][C:12]#[N:13])[CH2:6][C:7]([O:9][CH3:10])=[O:8]>CO.[Pd]>[CH3:10][O:9][C:7](=[O:8])[CH2:6][CH:5]([CH2:11][C:12]#[N:13])[CH2:4][C:3]([O:2][CH3:1])=[O:14]

Participants

4

Reactant 1

HCID 254955Dimethyl 3-(cyanomethylidene)pentanedioate

Product 1

HCID 59843343Dimethyl 3-(cyanomethyl)pentanedioateYield 52.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

To a solution of crude 3-cyanomethylene-pentanedioic acid dimethyl ester (403 g) in methanol (500 mL), 5% Pd—C was added and the mixture was stirred at room temperature for 4 days. The Pd—C was removed by filtration and the filtrate was concentrated under reduced pressure to give crude 3-cyanomethyl-pentanedioic acid dimethyl ester (212 g). The residue was purified by distillation to obtain 3-cyanomethyl-pentanedioic acid dimethyl ester (bp 130-150° C., 133 Pa) as a yellow oil. 1H NMR (200 MHz, CDCl3) δ ppm 2.46-2.61 (m, 5 H) 2.62-2.78 (m, 4 H) 3.71 (s, 6 H).

Workup

  1. customThe Pd—C was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-373dd5dd50af4cf7934801dd2e879c4b
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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