3-Butyn-1-OL → 4-[4-(Trifluoromethyl)phenyl]but-3-YN-1-OL

Participants

Reaction Conditions

Reaction Steps

The synthesis was performed following a procedure of Stara, Irena G.; Stary, Ivo; Kollarovic, Adrian; Teply, Filip; Saman, David; Fiedler, Pavel, Coupling reactions of halobenzenes with alkynes. The synthesis of phenylacetylenes and symmetrical or unsymmetrical 1,2-diphenylacetylenes, Collect. Czech. Chem. Commun. (1999), 64(4), 649-672. To a degassed (argon) solution of 5.0 g (17.83 mmol) 1-iodo-4-trifluoromethyl-benzene in 65 ml piperidine was added 1.03 g (0.89 mmol) Pd(PPh3)4 and 0.17 g (0.89 mmol) CuI. The reaction mixture was stirred at 50° C. for 10 min, then 2.03 ml (26.75 mmol) of but-3-yn-1-ol were added dropwise within 1 h. During the addition of but-3-yn-1-ol the oil bath was slowly heated to 80° C. starting after 30 min. The reaction mixture was stirred at this temperature for 3 h and then extracted with chilled aqueous 10% KHSO4/Et2O (three times). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated. Purification by flash-chromatography on silica gel (n-heptane/EtOAc 9:1 to 4:1) yielded 3.58 g of the title compound as a yellow solid.

Provenance & Evidence