Chlorotrimethylsilane → HCID 59243268, compound

HRID 2406502Notes

Reaction equation

HRID 2406502 reaction equation
[In].Br[CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C[Si](Cl)(C)C.[CH2:19]([CH:22]1[CH2:27][CH2:26][C:25](=[O:28])[CH:24]=[CH:23]1)[CH:20]=[CH2:21]>C1COCC1>[CH2:19]([CH:22]1[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH:23]1[CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:20]=[CH2:21]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 69637Diethyl bromomalonateHCID 5359967IndiumHCID 109535714-(2-Propenyl)-2-cyclohexen-1-one

Product 1

HCID 59243268HCID 59243268, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Indium (114.8 mg, 1.0 mmol), diethyl bromomalonate (359.0 mg, 1.5 mmol), and TMSCl (0.6 mL, 5.0 mmol) were added to (±)-4-(2-propenyl)-2-cyclohexen-1-one (0.120 mg, 1.0 mmol) in anhydrous THF (1 mL) at room temperature under nitrogen atmosphere. After 30 minutes of stirring the reaction was quenched with saturated NaHCO3. The aqueous layer was extracted with diethyl ether and the combined organics were washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The product was identified by mass spectrometry, (ESI, Pos) m/z 391 (M+23).

Workup

  1. customwas quenched with saturated NaHCO3
  2. extractionThe aqueous layer was extracted with diethyl ether
  3. washthe combined organics were washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23924346c0554a65aafc223c678ff183
Source dataset
uspto-grants-2014_08
Patent number
US08809373B2

Reaction notes

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