1: 71 percent / KHS, 18-crown-6 / ethane-1,2-diol / 2 h / 140 °C 2: 27 percent / p-TSA / acetone / Ambient temperature View Scheme

1: 1) N,N,N',N'-tetramethylethylenediamine, 2) n-BuLi, CuI / 1) a) ethyl ether, dry ice, acetone bath, b) -15 deg C, 45 min, 2) -15 deg C, 20 min, 3) -20 deg C, 24 h 2: 0.25 g / p-TSA / acetone / 18 h / Ambient temperature 3: 93 mg / 1.0 M NaOH / methanol / 2 h / Heating View Scheme