Pentane → HCID 54342566, compound

Participants

Reaction Conditions

Reaction Steps

6-Bromo-3-methyl-3,5-hexadienal (0.95 g; 5 mmol) dissolved in acetonitrile (25 cc) and pentane (25 cc) is introduced, under an argon atmosphere, into a 100-cc round flask fitted with a septum and a magnetic stirrer. Triethylamine (1 g; 10 mmol, i.e. 2 equivalents) is then added. After the mixture has been cooled to 0° C., bromotrimethylsilane (1.53 g; 2 equivalents) is added dropwise. The temperature is allowed to return to about 20° C. After 48 hours the reaction is complete. The acetonitrile phase is extracted with pentane (4×15 cc) under an argon atmosphere. After evaporation of the solvent and distillation, 6-bromo-3-methyl-1-trimethylsilyloxy-1,3,5-hexatriene (0.53 g) is obtained (b.p. 0.06 kPa=92°-95° C.). The yield is 46.8%. The structure of the product obtained is confirmed by the infrared spectrum and the proton nuclear magnetic resonance spectrum.

Provenance & Evidence