Pinacolone → Ethyl pivaloylacetate

HRID 437479Notes

Reaction equation

HRID 437479 reaction equation
[H-].[Na+].[CH3:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].[C:10](=O)([O:14]CC)[O:11][CH2:12][CH3:13]>CN(C)P(=O)(N(C)C)N(C)C>[CH2:12]([O:11][C:10](=[O:14])[CH2:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6])[CH3:13]

Participants

5

Reactant 3

HCID 6416PinacoloneHCID 7766Diethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 86950Ethyl pivaloylacetateYield 91%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

325 g of sodium hydride (80% solution in paraffin oil) were suspended in 2500 cc of diethyl carbonate and 500 cc of hexamethyl phosphoric acid triamide, 500 g of pinacolone (92%) were then slowly added dropwise at 45° to 50° C. and, on completion of the addition the reaction mixture was treated as described in 3 above. The yield was 91% of pivaloyl acetic acid ethyl ester.

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-9fb84386c8a44eeaaa1a3e2888fe81ed
Source dataset
uspto-grants-1977_06
Patent number
US04031130

Reaction notes

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