Methyl iodide → TERT-BUTYL 2-METHYL-3-OXOBUTANOATE

HRID 1364506Notes

Reaction equation

HRID 1364506 reaction equation
CI.[C:3]([O-])([O-])=O.[K+].[K+].[O:9]=[C:10]([CH3:19])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>CC(C)=O>[CH3:3][CH:11]([C:10](=[O:9])[CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15538Tert-butyl acetoacetate

Product 1

HCID 11745089TERT-BUTYL 2-METHYL-3-OXOBUTANOATEYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl iodide (6.86 mL, 1.1 eq) and K2CO3 (17.97 g, 1.3 eq) were added to an acetone (400 mL) solution of tert-butyl 3-oxobutanoate (15.82 g, 100 mmol) at room temperature. After 15 h, the mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate (300 mL), washed with water (30 mL) and brine (300 mL), dried (MgSO4) and concentrated. The crude residue was purified by silica gel chromatography (5-10% EtOAc-hexanes) to give tert-butyl 2-methyl-3-oxobutanoate as a colorless oil (9.56 g, 56%). MS found: (M+Na)+=195.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  4. washwashed with water (30 mL) and brine (300 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel chromatography (5-10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-f6cf00c00cf74bbba5243a31f2443d77
Source dataset
uspto-grants-2011_02
Patent number
US07888381B2

Reaction notes

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