Chlorotrimethylsilane → [(Bicyclo[2.2.1]hept-2-en-2-yl)oxy](trimethyl)silane

HRID 2058286Notes

Reaction equation

HRID 2058286 reaction equation
C[Li].C(NC(C)C)(C)C.[CH2:10]1[CH:14]2[CH2:15][C:16](=[O:17])[CH:12]([CH2:13]2)[CH2:11]1.Cl[Si:19]([CH3:22])([CH3:21])[CH3:20]>C(OCC)C>[CH3:20][Si:19]([CH3:22])([CH3:21])[O:17][C:16]1[CH:12]2[CH2:13][CH:14]([CH:15]=1)[CH2:10][CH2:11]2

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 143502[(Bicyclo[2.2.1]hept-2-en-2-yl)oxy](trimethyl)silane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-78 °C

Procedure

Methyllithium in diethyl ether (141 ml of 1.8 M solution) was added dropwise to a solution of 27.6 g of diisopropylamine in 38 ml of dry diethyl ether. The resulting solution was cooled to -78° C. and 19.7 g of norcamphor in 20 ml of diethyl ether were added dropwise. The reaction mixture was warmed to 0° C. and 46 ml of chlorotrimethylsilane were added. The reaction mixture was warmed to 25° C., stirred for 30 minutes, extracted with cold 5% aqueous sodium bicarbonate, dried (over MgSO4) and then distilled to give 22.3 g of 2-trimethylsiloxybicyclo[2.2.1]-hept-2-ene as a colorless liquid: bp 70°-73° C. (14 mm).

Workup

  1. temperatureThe reaction mixture was warmed to 0° C.
  2. temperatureThe reaction mixture was warmed to 25° C.
  3. extractionextracted with cold 5% aqueous sodium bicarbonate
  4. dry with materialdried (over MgSO4)
  5. distillationdistilled

Sources & evidence

ORD record
ord-d23a351033424139aa275dab4091d425
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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