Sodium Hydroxide → Methyl 3-methyl-4-oxobutanoate

HRID 1732276

Reaction equation

HRID 1732276 reaction equation
[CH3:1][CH:2]([CH2:8][N+]([O-])=O)[CH2:3][C:4]([O:6][CH3:7])=[O:5].C[O-].[Na+].[OH:15]P([O-])(O)=O.[K+].[OH-].[Na+]>CO.[Cl-].[Cl-].[Ti+2].CCOCC>[CH3:1][CH:2]([CH:8]=[O:15])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 516951Monobasic potassium phosphateHCID 10942334Sodium MethoxideHCID 13633418Methyl 3-methyl-4-nitrobutanoate

Product 1

HCID 11804788Methyl 3-methyl-4-oxobutanoate

Reagents, catalysts & solvents 3

HCID 10290777Titanium(2+);dichlorideCatalystHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of methyl 3-methyl-4-nitrobutanoate (24.55 g) in methanol (10 ml) is added dropwise to a solution of sodium methoxide (6.37 g) in methanol (250 ml) at room temperature under nitrogen. The resulting mixture is stirred for one hour, added to a mixture of 20% titanous chloride (170 ml), and pH 7 buffer (potassium phosphate monobasic--sodium hydroxide buffer) solution (340 ml) and stirred for 30 minutes. The mixture is then treated with ether (1 l). The organic phase is separated, dried (Na2SO4) and evaporated in vacuo to give the crude product. The crude material is purified by column chromatography on silica gel (300 g, 2% ethyl acetate in hexane) to give methyl 3-methyl-4-oxo-butanoate as a colorless liquid. This material is used directly in the next step.

Workup

  1. stirringstirred for 30 minutes
  2. customThe organic phase is separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give the crude product
  6. customThe crude material is purified by column chromatography on silica gel (300 g, 2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-123f24d62710476aac4b17e30b18b4a0
Source dataset
uspto-grants-1980_12
Patent number
US04237054

Linked notes

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