Triethylamine → 6-Trimethylsilanylethynyl-naphthalene-1-carboxylic acid methyl ester

Participants

Reaction Steps

A solution of 15.6 ml (113 mMol) ethynyl-trimethylsilane (Fluka; Buchs/Switzerland) and 15.7 ml (113 mMol) Et3N in 250 ml degassed DMF is added to 34 g (102 mMol) 6-trifluoromethanesulfonyloxy-naphthalene-1-carboxylic acid methyl ester, 1.0 g (5.2 mMol) CuI and 5.0 g (7.1 mMol) Pd(PPh3)2Cl2 in 250 ml of degassed DMF. After 15 h at rt, the mixture is concentrated partially in vacuo at 40° C. and the residue re-dissolved in sat. NaHCO3 solution and EtOAc. The aq. phase is separated off and extracted twice with EtOAc. The organic layer is washed twice with sat. NaHCO3 solution, water/sat. NaHCO3 solution 1:1 and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/EtOAc 199:1) gives the title compound as an oil: MS: [M+1]+=283; TLC(hexane/EtOAc 19:1): Rf=0.22.

Provenance & Evidence