Cyclohexanone → HCID 11084070, compound

HRID 1835754Notes

Reaction equation

HRID 1835754 reaction equation
CC(C)([O-])C.[K+].[C:7]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:14](Br)[CH2:15][CH:16]=[CH2:17].CCOC(C)=O>C1(C)C=CC=CC=1>[CH2:17]([CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C:7]1=[O:13])[CH2:16][CH:15]=[CH2:14]

Participants

6

Reactant 4

HCID 7967CyclohexanoneHCID 8857Ethyl AcetateHCID 21241Homoallyl bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 11084070HCID 11084070, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Ex-18a) A suspension of potassium t-butoxide in toluene cooled to 0° C. in an ice bath under N2 is treated with cyclohexanone. To the reaction mixture is slowly added 3-butenyl bromide. The reaction is warmed to room temperature. The reaction is then poured into EtOAc and washed once with 10% potassium hydrogen sulfate. The organic solution is then washed with brine, dried over magnesium sulfate, and the solvent evaporated under reduced pressure to afford 2-(3-butenyl) cyclohexanone.

Workup

  1. temperatureThe reaction is warmed to room temperature
  2. washwashed once with 10% potassium hydrogen sulfate
  3. washThe organic solution is then washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-2821b8840ce348a6ad0203d5f827e5da
Source dataset
uspto-grants-2004_08
Patent number
US06774126B2

Reaction notes

Loading…