2-Methyl-3-butyn-2-ol → HCID 131716781, compound

Participants

Reaction Steps

39 g (0.075 mol) of 1,2-bis-(4-bromophenoxy)-3,3,4,4,5,5-hexafluorocyclopent-1-ene (obtained according to Example 1), 32 g (0.38 mol) of 2-methyl-3-butin-2-ol, 211 mg of PdCl2 (PPh3)2, 230 mg of CuI and 630 mg of triphenylphosphine were added under nitrogen to 100 ml of triethylamine. After heating to reflux for 24 hours, the reaction mixture was filtered and the filtrate was concentrated in vacuo. Recrystallization of the residue resulting here from n-hexane/ethyl acetate gave 19.1 g of product, which corresponds to 48% of theory, having a melting point of 108° to 113° C. The 1H NMR spectrum showed characteristic bands at 1.59 ppm, 6.63 ppm and 7.2 ppm, measured against tetramethylsilane as internal standard.

Provenance & Evidence