Isovaleryl chloride → 2-Methyldec-5-yn-4-one

Participants

Reaction Conditions

Reaction Steps

21.6 g of AlCl3 (0.162 moles) in 65 mL of CCl4 are cooled to 2° C. and 19.7 mL of isovaleroyl chloride (0.162 moles) in 30 mL of CCl4 are added dropwise. 25 g of trimethylsilylhexyne (0.162 moles) in 30 mL of CCl4 are then added dropwise. The mixture is stirred for 1 h at 2° C. and for 24 h at ambient temperature. It is poured into 200 mL of 1:3 37% HCl/ice, stirred for 1 h, the phases are separated and the aqueous phase is extracted with CH2Cl2. The combined organic phases are washed to neutrality, dried with Na2SO4 and evaporated. 27 g of product are obtained, which are used in the subsequent step without further purification. Formula: C11H18O (m.w. 166.27). Quantitative yield. IR (film) 2956; 2209; 1670 cm−1.

Provenance & Evidence