2-Isopentylcyclopent-2-en-1-one → 2-(3-Methyl-butyl)-3-vinyl-cyclopentanone

HRID 61332

Reaction equation

HRID 61332 reaction equation
[CH:1]([Mg]Cl)=[CH2:2].[CH3:5][CH:6]([CH3:15])[CH2:7][CH2:8][C:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH:13]=1>C(O)(=O)C>[CH3:5][CH:6]([CH3:15])[CH2:7][CH2:8][CH:9]1[CH:13]([CH:1]=[CH2:2])[CH2:12][CH2:11][C:10]1=[O:14]

Participants

4

Reactant 2

HCID 1224642-Isopentylcyclopent-2-en-1-oneHCID 178461836HCID 178461836, compound

Product 1

HCID 897051562-(3-Methyl-butyl)-3-vinyl-cyclopentanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-25 °C

Procedure

Vinylmagnesium chloride (H2CHCClMg, 1 L) and cuprous chloride were charged to a dried flask under nitrogen and cooled to −25° C. with a dry ice bath. The resulting mixture was fed with 2-(3-methyl-butyl)-cyclopent-2-enone (226 g, 1.49 mol, obtained as detailed above) slowly for over 4 hours, aged for another 4 hours, and allowed to warm to 0° C. The reaction mixture was then poured into acetic acid solution and washed to neutral with saturated Na2CO3 solution. The distillation process provided the product 2-(3-methyl-butyl)-3-vinyl-cyclopentanone.

Workup

  1. temperatureto warm to 0° C
  2. washwashed to neutral with saturated Na2CO3 solution

Sources & evidence

ORD record
ord-09352ae357f04cdba49ce68030613fe1
Source dataset
uspto-grants-2016_09
Patent number
US09441185B2

Linked notes

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