Methyl 3-hydroxypivalate → Methyl 2,2-dimethyl-3-oxopropanoate

HRID 1877778Notes

Reaction equation

HRID 1877778 reaction equation
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:8][C:3]([CH3:9])([CH:2]=[O:1])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 84152Methyl 3-hydroxypivalateHCID 159087Triacetoxyperiodinane

Product 1

HCID 11137194Methyl 2,2-dimethyl-3-oxopropanoateYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methyl 3-hydroxy-2,2-dimethylpropanoate (33 g, 250 mmol) to Dess-Martin periodinane (106 g, 250 mmol) suspended in DCM (1000 mL) at 0° C. and stir at room temperature for 18 h. Filter the reaction mixture through a celite bed and concentrate the filtrate. Wash the concentrated filtrate with pentane (2×200 mL). Separate the pentane layer and concentrate in vacuo to give methyl 2,2-dimethyl-3-oxo-propanoate (31.93 g, quantitative). 1H NMR (d6-DMSO) δ 9.59 (s, 1H), 3.67 (s, 3H), 1.26 (s, 6H).

Workup

  1. filtrationFilter the reaction mixture through a celite bed
  2. concentrationconcentrate the filtrate
  3. washWash the concentrated filtrate with pentane (2×200 mL)
  4. customSeparate the pentane layer
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-0e8fdc1971c84adf92ad9e22eb74caa4
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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