Water → Methyl 4-(Pyridin-4-yl)butanoate

HRID 618158Notes

Reaction equation

HRID 618158 reaction equation
[CH3:1][O:2][C:3]([CH:5]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)C(OC)=O)=[O:4].O.[Na+].[Cl-].CN(C=O)C>CCOC(C)=O>[N:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 21699793Dimethyl 2-(2-(pyridin-4-yl)ethyl)malonate

Product 1

HCID 12114953Methyl 4-(Pyridin-4-yl)butanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of diester 10-3 (19.0 g, 80.1 mmol), H2O (1.45 ml, 80.1 mmol), NaCl (10.5 g, 160.2 mmol) and DMF was heated to 170° C. for 18 h. The reaction was diluted with EtOAc and then washed with sat. NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 60% EtOAc/hexanes) afforded ester 10-4 as a brown oil.

Workup

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-51ac67d604ac434eb10ccba9356bff64
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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