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

HRID 1894760Notes

Reaction equation

HRID 1894760 reaction equation
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=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 178418287HCID 178418287, compound

Product 1

HCID 11137194Methyl 2,2-dimethyl-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-hydroxy-2,2-dimethylpropanoate (8.6 g, 65.1 mmol) in 100 mL DCM was cooled to 0° C. under N2. PCC (24.8 g, 115.2 mmol) was added portionwise over several minutes. The mixture was allowed to gradually warm to room temperature and was stirred overnight. The mixture was filtered through silica gel. Enough Celite is added to the remaining oil so that all is adsorbed. This is added to the top of a silica pad and this is washed with about 1.5 L DCM. The solution is then carefully concentrated in vacuo, maintaining the water bath at about 30° C. to obtain methyl 2,2-dimethyl-3-oxopropanoate as a clear colorless oil. 1H (300 MHz, CDCl3, δ) 9.60 (s, 1H), 3.70 (s, 3H), 1.29 (s, 6H).

Workup

  1. filtrationThe mixture was filtered through silica gel
  2. additionEnough Celite is added to the remaining oil so that
  3. additionThis is added to the top of a silica pad
  4. washthis is washed with about 1.5 L DCM
  5. concentrationThe solution is then carefully concentrated in vacuo
  6. temperaturemaintaining the water bath at about 30° C.

Sources & evidence

ORD record
ord-4efaaf48c13c4d4981caf9341c05455f
Source dataset
uspto-grants-2013_08
Patent number
US08513291B2

Reaction notes

Loading…