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

HRID 1689750Notes

Reaction equation

HRID 1689750 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-bcf4c942452542b2835469abebe17bbc
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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