4-Methyl-2-oxovaleric acid → Methyl 4-methyl-2-oxopentanoate

HRID 2261726Notes

Reaction equation

HRID 2261726 reaction equation
[CH3:1][CH:2]([CH3:9])[CH2:3][C:4](=[O:8])[C:5]([OH:7])=[O:6].Cl[Si](C)(C)[CH3:12]>CO.COC(OC)(C)C>[CH3:12][O:6][C:5](=[O:7])[C:4](=[O:8])[CH2:3][CH:2]([CH3:9])[CH3:1]

Participants

5

Reactant 2

HCID 704-Methyl-2-oxovaleric acidHCID 6397Chlorotrimethylsilane

Product 1

HCID 546077Methyl 4-methyl-2-oxopentanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

To a solution of 4-methyl-2-oxo-pentanoic acid (3.4 g, 26 mmol) in methanol (12 mL) and 2,2-dimethoxypropane (48 mL) is added chlorotrimethylsilane (0.38 mL). The reaction mixture is stirred at ambient temperature overnight. The reaction mixture is concentrated under reduced pressure to give the title compound as an oil, (3.8 g, quant.). 1H NMR (400 MHz, CDCl3): δ 3.86 (s, 3H), 2.72 (d, 2H), 2.16 (m, 1H), 0.96 (d, 6H).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-9c94aee87db64cf4a8fffb905caea73e
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…