4-Acetylpyridine → 4,4-Dimethoxy-1-pyridin-4-yl-butane-1,3-dione

HRID 1454292Notes

Reaction equation

HRID 1454292 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:20][O:21][CH:22]([O:27][CH3:28])[C:23](OC)=[O:24]>O1CCCC1.CCCCCC>[CH3:20][O:21][CH:22]([O:27][CH3:28])[C:23](=[O:24])[CH2:2][C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 142824-AcetylpyridineHCID 66647Acetic acid, 2,2-dimethoxy-, methyl esterHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 178745444,4-Dimethoxy-1-pyridin-4-yl-butane-1,3-dione

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 4-acetylpyridine (12 g) in dry tetrahydrofuran (500 ml), under nitrogen and at −60° C., was treated with a solution of lithium bis(trimethylsilyl)amide in hexane (200 ml, 1M). The mixture was allowed to warm to −40° C. then treated with methyl dimethoxyacetate (12 ml). After standing at room temperature for 16 hours the reaction mixture was evaporated and the residue was triturated with diethyl ether to give the title compound as a yellow solid (22 g).

Workup

  1. customthe reaction mixture was evaporated
  2. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-56ca476c8e0c44778a79d35ca513aeec
Source dataset
uspto-grants-2009_01
Patent number
US07479501B2

Reaction notes

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