Ethyl valerate → Octa-1,2-dien-4-one
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
Product 1
Reagents, catalysts & solvents 1
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
- washThe ether layer is washed with brine
- additiontreated with hydroquinone
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6c329e36c1e741b9b076e225f0e0db3b
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04233453
Reaction notes
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