Pinacolone → Methyl pivaloylacetate

HRID 437480

Reaction equation

HRID 437480 reaction equation
[H-].[Na+].[CH3:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].[C:10](=O)([O:13]C)[O:11][CH3:12]>CN(C)P(=O)(N(C)C)N(C)C>[CH3:12][O:11][C:10](=[O:13])[CH2:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 6416PinacoloneHCID 12021Dimethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 99597Methyl pivaloylacetateYield 83.5%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

60 g of sodium hydride were suspended in 450 cc of dimethyl carbonate and 100 cc of hexamethyl phosphoric acid triamide. 100 g of pinacolone (92%) were added slowly at 45° C and on completion of the addition, the reaction mixture was processed as described in 3 above. The yield was 83.5% of pivaloyl acetic acid methyl ester.

Sources & evidence

ORD record
ord-0fb85a1d813f4f5ea5765711fed7dda6
Source dataset
uspto-grants-1977_06
Patent number
US04031130

Linked notes

Loading…