Pivalaldehyde → 2,2-Dimethylhex-5-en-3-ol
Reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH:3]=[O:4].[CH2:7]([Mg]Br)[CH:8]=[CH2:9]>C(OCC)C>[CH3:1][C:2]([CH3:6])([CH:3]([OH:4])[CH2:9][CH:8]=[CH2:7])[CH3:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of trimethylacetaldehyde (10.2 mL, 90.9 mmol) in diethyl ether (200 mL) at 0° C. was added allylmagnesium bromide (100 mL, 1M in ether). The reaction mixture was stirred at 0° C. for 1 hour. The resulting mixture was quenched with saturated ammonium chloride and extracted with diethyl ether. The organic extracts were washed with brine, dried over Na2SO4 and filtered. The solvent was carefully removed under reduced pressure to afford the title compound;
Workup
- customThe resulting mixture was quenched with saturated ammonium chloride
- extractionextracted with diethyl ether
- washThe organic extracts were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe solvent was carefully removed under reduced pressure
Sources & evidence
- ORD record
- ord-915c196d2c344ef28620e5ea6f9851b6
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403810B2
Reaction notes
Loading…