Sodium Acetate → HCID 68497272, compound

HRID 1712340Notes

Reaction equation

HRID 1712340 reaction equation
[C:1]([O-])(=[O:3])[CH3:2].[Na+].[C:6]([CH2:8][C:9]1[C:17]2[O:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)#[N:7]>C(OC(=O)C)(=O)C.[Ni]>[C:1]([NH:7][CH2:6][CH2:8][C:9]1[C:17]2[O:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 68505218HCID 68505218, compound

Product 1

HCID 68497272HCID 68497272, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 1.07 g of sodium acetate, 2.00 g of methyl 7-cyanomethylbenzofuran-2-carboxylate in 10.4 ml of acetic anhydride is hydrogenated in the presence of 0.22 g of Raney nickel at 50° C. over 5 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The residue is dissolved in ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution, water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (6:1 EtOAc-heptane); Rt=3.23.

Workup

  1. filtrationThe reaction mixture is clarified by filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogencarbonate solution, water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3f030a4254ae46ccac21b9d772a567c3
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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