Methanol → Dimethyl 2-(2-(pyridin-4-yl)ethyl)malonate

HRID 618157Notes

Reaction equation

HRID 618157 reaction equation
[Na].CO.[C:4]([O:11][CH3:12])(=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[CH2:14]>CCOC(C)=O>[CH3:9][O:8][C:6]([CH:5]([CH2:14][CH2:13][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[C:4]([O:11][CH3:12])=[O:10])=[O:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 75024-VinylpyridineHCID 7943Dimethyl malonateHCID 5360545Sodium

Product 1

HCID 21699793Dimethyl 2-(2-(pyridin-4-yl)ethyl)malonateYield 57.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of elemental sodium (20 g, 840 mmol) and CH3OH (600 ml) was added dimethyl malonate 10-1 (135 ml, 1120 mmol). After 5 minutes, 4-vinyl pyridine 10-2 (15.3 ml, 140 mmoles) was added and the solution was heated to 50° C. for 18 h. The reaction was diluted with EtOAc and then washed with sat NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatoraphy (silica, 60% EtOAc/hexanes) furnished the diether 10-3 (19.1 g) as a yellow oil.

Workup

  1. washwashed
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2e05ac15b2134f79a56a03d470d5ffec
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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