Allyl bromide → 4-(Allyloxy)-4-methylpent-1-ene
Reaction equation
[H-].[Na+].[CH3:3][C:4]([OH:9])([CH2:6][CH:7]=[CH2:8])[CH3:5].[CH2:10](Br)[CH:11]=[CH2:12]>CN(C)C=O>[CH2:12]([O:9][C:4]([CH3:5])([CH3:3])[CH2:6][CH:7]=[CH2:8])[CH:11]=[CH2:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of sodium hydride (60%, 24 g, 60 mmol) in N,N-dimethylformamide (150 mL) at 0° C. was slowly added 2-methylpent-4-en-2-ol (20.0 g, 200 mmol). After 1 hour at 0° C., allyl bromide (48.0 g 400 mmol) was slowly added at 0˜5° C., and the reaction mixture was stirred at 0° C. for another 1 hour. The reaction was quenched with aq. ammonium chloride solution and extracted with tert-butyl methyl ether. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (44 g, crude) as a yellow oil, which was directly used in the next step without further purification.
Workup
- customThe reaction was quenched with aq. ammonium chloride solution
- extractionextracted with tert-butyl methyl ether
- washThe combined organic layers were washed with water and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-bfa0aeb73a3441f384d12a0515351cc1
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434700B2
Reaction notes
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