Chlorotrimethylsilane → HCID 10487695, compound

HRID 2404592Notes

Reaction equation

HRID 2404592 reaction equation
[CH:1]12[CH2:7][CH:6]1[CH2:5][CH2:4][CH2:3][C:2]2=[O:8].[Li+].CC([N-]C(C)C)C.[CH3:17][Si:18](Cl)([CH3:20])[CH3:19]>C1COCC1>[CH:1]12[CH2:7][CH:6]1[CH2:5][CH2:4][CH:3]=[C:2]2[O:8][Si:18]([CH3:20])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 282471Bicyclo[4.1.0]heptan-2-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 10487695HCID 10487695, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add dropwise bicyclo[4.1.0]heptan-2-one (43.3 g, 0.393 mol) in dry THF (50 mL) to a solution of LDA (237 mL, 0.472 mol) in THF (500 mL). Stir the reaction mixture for 30 min and then add dropwise TMSCl (64.2 g, 0.59 mol) to the reaction mixture. Stir the resultant solution for additional 1 hour. Pour the mixture into ice water (92 mL) and extract the aqueous mixture with EtOAc (100 mL×3). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford crude (bicyclo[4.1.0]hept-2-en-2-yloxy)-trimethyl-silane (68.0 g, 95.0%) as yellowish oil, MS (m/z): 181 (M−1).

Workup

  1. extractionextract the aqueous mixture with EtOAc (100 mL×3)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd6cf6a6d3cb4a54840612c8090560d6
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

Loading…