Chlorotrimethylsilane → 3-(Propan-2-yl)cyclopentan-1-one

HRID 1408739Notes

Reaction equation

HRID 1408739 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.Cl[Si](C)(C)C.CN(P(N(C)C)(N(C)C)=O)C.[CH:23]([Mg]Br)([CH3:25])[CH3:24]>C1COCC1>[CH:23]([CH:3]1[CH2:4][CH2:5][C:1](=[O:6])[CH2:2]1)([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 12679HexamethylphosphoramideHCID 135882-Cyclopenten-1-oneHCID 178418365HCID 178418365, compound

Product 1

HCID 125705723-(Propan-2-yl)cyclopentan-1-oneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of cyclopent-2-enone (1.5 mL, 18.27 mmol), CuBr—SMe2 (188 mg, 0.91 mmol), chlorotrimethylsilane (4.59 mL, 36.54 mmol) and HMPA (6.55 g, 36.54 mmol) in THF (30 mL) was added isopropylmagnesium bromide (36.54 mL, 1 M in THF) at −70° C. After stirring for 1 h at −70° C., the reaction mixture was quenched with HCl (10%). The mixture was extracted with Et2O. The organic layer was washed with aqueous NaHCO3 and brine. After dried over Na2SO4, the organic layer was concentrated to give 3-isopropylcyclopentanone (4 g, 100%).

Workup

  1. customthe reaction mixture was quenched with HCl (10%)
  2. extractionThe mixture was extracted with Et2O
  3. washThe organic layer was washed with aqueous NaHCO3 and brine
  4. dry with materialAfter dried over Na2SO4
  5. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-f51804cce5ef42489c392907d358750f
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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