Chlorotrimethylsilane → HCID 20541498, compound

Participants

Reaction Steps

To a solution of 400 mg 3-trimethylsilyloxy-1,4-pentadiene in 3 ml of tetrahydrofuran at -78° under argon was added a solution of 2.3 ml of sec-butyllithium in cyclohexane and the solution stirred for 15 minutes. Then, a solution of 275 mg. of 2,6,6-trimethylcyclohexa-2,4-dienone in 1 ml of tetrahydrofuran was added. After 5 minutes, 332 mg of trimethylsilyl chloride in 2 ml of hexamethylphosphoric acid triamide was added and the mixture left for 1 hour at -78°. After working up as in Example 1(a) the crude product mixture was diluted with 20 ml of methanol cooled to 0° and 224 mg of potassium fluoride were added. After 1 hour at 0°-5°, the mixture was poured into saturated aqueous NH4Cl solution and extracted with ether. Chromatography (SiO2, toluene) of the evaporated extract gave 329 mg of 1-[3-oxo-pent-4 -en-1-yl]-1-trimethylsilyloxy-2,6,6-trimethylcyclohexa-2,4-diene (56% yield) characteristics as above.

Provenance & Evidence