Nonanoyl chloride → 1-(Trimethylsilyl)undec-1-yn-3-one

Participants

Reaction Steps

To 500 ml of CH2Cl2 was added 53 ml (294 mmol) of nonanoyl chloride and 50 g (293.4 mmol) of bis(trimethylsilyl)acetylene. The reaction mixture was cooled in an ice bath and 40 g (300 mmol) of AlCl3 was added portionwise with stirring over 1/2 hour. After stirring for an additional hour the reaction mixture was quenched with ice. Water was added to the reaction mixture and it was extracted 3× with 200 ml aliquots of diethyl ether. The combined extracts were washed 2× with 50 ml aliquots of saturated NaHCO3, 1 × with brine, and then dried (MgSO4). The solvent was removed in vacuo to give a brown oil which was used without further purification.

Provenance & Evidence