Ethyl valerate → Octa-1,2-dien-4-one

HRID 848889Notes

Reaction equation

HRID 848889 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 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-73585d81301b40f0bb0735feccbc1603
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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