Nonanoyl chloride → 1-(Trimethylsilyl)undec-1-yn-3-one
Reaction equation
[C:1](Cl)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH3:12][Si:13]([C:16]#[C:17][Si](C)(C)C)([CH3:15])[CH3:14].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:12][Si:13]([CH3:15])([CH3:14])[C:16]#[C:17][C:1](=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.