Sodium Acetate → HCID 9862147, compound

HRID 1167623Notes

Reaction equation

HRID 1167623 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][N:8]([CH2:18][C:19]#[N:20])[C:7]=2[CH:21]=1.[C:22]([O-])(=[O:24])[CH3:23].[Na+]>C(OC(=O)C)(=O)C.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][N:8]([CH2:18][CH2:19][NH:20][C:22](=[O:24])[CH3:23])[C:7]=2[CH:21]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 22993341HCID 22993341, compound

Product 1

HCID 9862147HCID 9862147, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

The compound obtained in Step D (350 mg; 1.25 mmol) is dissolved in a Parr reactor with acetic anhydride. Raney nickel (30% by weight, 115 mg) and sodium acetate (1.5 eq.; 1.87 mmol; 154 mg) are then added. The mixture is left at 50° C. for 16 hours under a hydrogen pressure of 40 psi. After returning to ambient temperature, the solution is filtered over Celite and the filtrate is evaporated. The crude reaction product is purified by flash chromatography on silica gel (eluant: PE/AcOEt (1/9)). The title product is obtained in the form of white crystals and is recrystallised from an Et2O/i-PrOH (6/4) mixture.

Workup

  1. customAfter returning to ambient temperature
  2. filtrationthe solution is filtered over Celite
  3. customthe filtrate is evaporated
  4. customThe crude reaction product
  5. customis purified by flash chromatography on silica gel (eluant: PE/AcOEt (1/9))

Sources & evidence

ORD record
ord-655eec7591fa41ba9a42ee02b391d76c
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

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