Dimethyl oxalate → Ethyl 4-(6-methyl-3-pyridyl)-2,4-dioxobutanoate

HRID 1171081Notes

Reaction equation

HRID 1171081 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)(=[O:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].O1CCC[CH2:22]1.[C:26]([O:32]C)(=O)[C:27]([O:29][CH3:30])=[O:28].Cl.O1CCOCC1>O1CCCC1>[CH3:10][C:7]1[N:8]=[CH:9][C:4]([C:1](=[O:3])[CH2:2][C:26](=[O:32])[C:27]([O:29][CH2:30][CH3:22])=[O:28])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 11120Dimethyl oxalateHCID 952923-Acetyl-6-methylpyridineHCID 204431481,4-Dioxane hydrochlorideHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23143403Ethyl 4-(6-methyl-3-pyridyl)-2,4-dioxobutanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At −78° C., a tetrahydrofuran (5 ml) solution of 5-acetyl-2-picoline (583 mg) was added to a tetrahydrofuran (15 ml) solution of 1 N lithium hexamethyldisilazide/tetrahydrofuran solution (5.2 ml), and stirred at the same temperature for 1 hour. At −78° C., dimethyl oxalate (701 μl) was added to the reaction liquid, and stirred at room temperature for 1 hour. 4 N hydrogen chloride/dioxane solution (4 ml) was added to the reaction liquid, and concentrated under reduced pressure to obtain a crude product of the entitled compound.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98e579a05ecf4d00ba816fa58c4b447d
Source dataset
uspto-grants-2010_11
Patent number
US07829586B2

Reaction notes

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