Pivalaldehyde → 2,2-Dimethylhex-5-en-3-ol

HRID 1478218Notes

Reaction equation

HRID 1478218 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

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

  1. customThe resulting mixture was quenched with saturated ammonium chloride
  2. extractionextracted with diethyl ether
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. 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

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