3,3-Dimethylcyclopentan-1-one → 3,3-Dimethyl-1-vinylcyclopentanol

HRID 516275Notes

Reaction equation

HRID 516275 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[CH3:5][C:6]1([CH3:12])[CH2:10][CH2:9][C:8](=[O:11])[CH2:7]1>C1COCC1>[CH3:5][C:6]1([CH3:12])[CH2:10][CH2:9][C:8]([CH:1]=[CH2:2])([OH:11])[CH2:7]1

Participants

4

Reactant 2

HCID 6431023,3-Dimethylcyclopentan-1-oneHCID 178418507HCID 178418507, compound

Product 1

HCID 806985423,3-Dimethyl-1-vinylcyclopentanolYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
7.5 °C

Procedure

The reactor was charged with vinylmagnesium bromide (0.6M in THF, 245 ml, 147 mmol) and the solution was cooled to 5-10° C. 3,3-Dimethylcyclopentanone (2a, 15.0 g, 134 mmol) in THF (50 ml) was added over 10 minutes while keeping the temperature of the reaction mixture between 5-10° C. by means of an ice bath. The mixture was stirred for 30 minutes, then quenched with 10% AcOH (150 ml) and extracted with hexane (2×100 ml). The combined organic phases were washed with water, dried (MgSO4), concentrated and distilled bulb-to-bulb to afford 3a (14.3 g, 76% yield) as a colorless liquid.

Workup

  1. custombetween 5-10° C.
  2. customquenched with 10% AcOH (150 ml)
  3. extractionextracted with hexane (2×100 ml)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. distillationdistilled bulb-to-bulb

Sources & evidence

ORD record
ord-adbbbd6856f740de87ec38f7e05ccc6c
Source dataset
uspto-grants-2015_08
Patent number
US09109186B2

Reaction notes

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