Ethyl valerate → Ethyl 3-oxo-2-propylheptanoate

HRID 1984794Notes

Reaction equation

HRID 1984794 reaction equation
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][CH2:5][CH2:6][CH3:7]>C1(C)C=CC=CC=1>[CH2:5]([CH:4]([C:3]([CH2:4][CH2:5][CH2:6][CH3:7])=[O:8])[C:3]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 10882Ethyl valerateHCID 24758Sodium hydride

Product 1

HCID 13421737Ethyl 3-oxo-2-propylheptanoateYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mechanically stirred suspension of sodium hydride (16.2 g of 60% dispersion in mineral oil) in 400 mL of anhydrous toluene was treated dropwise with ethyl pentanoate (50.0 g) at room temperature under nitrogen atmosphere. Upon completion of the addition, the reaction mixture was refluxed for 5 h and then cooled to room temperature, quenched by pouring onto a mixture of ice and 10% aqueous hydrochloric acid, and extracted with chloroform. The combined organic phases were washed with aqueous solution of potassium bicarbonate, then with water, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator, and distilled in vacuum to give 32.0 g (79%) of the title compound.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was refluxed for 5 h
  3. customquenched
  4. additionby pouring onto a mixture of ice and 10% aqueous hydrochloric acid
  5. extractionextracted with chloroform
  6. washThe combined organic phases were washed with aqueous solution of potassium bicarbonate
  7. dry with materialwith water, dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator
  10. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-aa389249ca324c02aaa7fe5abb21c445
Source dataset
uspto-grants-2009_06
Patent number
US07544748B2

Reaction notes

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