Chlorotrimethylsilane → HCID 68291626, compound

HRID 2404601Notes

Reaction equation

HRID 2404601 reaction equation
[CH2:1]1[CH:9]2[CH:4]([C:5](=[O:10])[CH2:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.[CH3:19][Si:20](Cl)([CH3:22])[CH3:21]>C1COCC1>[CH2:1]1[CH:9]2[CH:4]([C:5]([O:10][Si:20]([CH3:22])([CH3:21])[CH3:19])=[CH:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 228144Octahydro-4H-inden-4-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 68291626HCID 68291626, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add dropwise hexahydro-1H-inden-4(2H)-one (1.6 g, 11.6 mmol) in dry THF (5 mL) to a solution of LDA (23.2 mL, 23.2 mmol) in THF (30 mL). Stir the reaction mixture for 30 min and then add dropwise TMSCl (3.5 g, 32.0 mmol) to the reaction mixture. Stir the resultant solution for additional 1 hour. Pour the mixture into ice water (50 mL) and extract the aqueous mixture with EtOAc (50 mL×3). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford crude (2,3,3a,6,7,7a-hexahydro-1H-inden-4-yloxy)trimethylsilane (2.45 g, 100%) as yellowish oil, MS (m/z): 209 (M−1).

Workup

  1. extractionextract the aqueous mixture with EtOAc (50 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-b23e74ca43dc4b1fbbf6b1aeefb56c34
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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