Ethyl valerate → Octa-1,2-dien-4-one

HRID 224698

Reaction equation

HRID 224698 reaction equation
[CH2:1]([Mg]Br)[C:2]#[CH:3].[C:6](OCC)(=[O:11])[CH2:7][CH2:8][CH2:9][CH3:10]>CCOCC>[CH2:3]=[C:2]=[CH:1][C:6](=[O:11])[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 10882Ethyl valerateHCID 178455849HCID 178455849, compound

Product 1

HCID 11194330Octa-1,2-dien-4-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 0.50 moles of propargylmagnesium bromide in 340 ml. of ether at -78° C. is added a solution of 65.2 g. (0.50 moles) of the ethyl valerate in 100 ml. of ether during 60 minutes. The solution is stirred at -78° C. for 30 minutes and then hydrolyzed by pouring onto a mixture of ice and ether. The ether layer is washed with brine, treated with hydroquinone, dried over magnesium sulfate, and concentrated.

Workup

  1. washThe ether layer is washed with brine
  2. additiontreated with hydroquinone
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6c329e36c1e741b9b076e225f0e0db3b
Source dataset
uspto-grants-1980_11
Patent number
US04233453

Linked notes

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