oxalyl dichloride; Bis-lt;(p-methoxy)phenylgt;cyclopropenon in dichloromethane T=30°C; 1 h; Inert atmosphere;

pyridine in (2S)-N-methyl-1-phenylpropan-2-amine hydrate

1: n-BuLi / tetrahydrofuran / -78 °C 2: CCl4; PPh3 View Scheme

2: SOCl2 View Scheme

(i) nBuLi, (ii) /BRN= 1209228/, (iii) SOCl2, CHCl3; Multistep reaction;

dichloromethane, 24 h, r.t.; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

1,8-diazabicyclo[5.4.0]undec-7-ene; cobalt(II) dibromide in acetonitrile T=80°C; Inert atmosphere;

[Cu(N,N′-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene)Cl]; potassium carbonate in N,N-dimethyl-formamide T=60°C; P=11251.1 Torr; 24 h; Autoclave;

potassium carbonate in acetonitrile T=80°C; 2 h;

1: 90 percent / n-Bu4NI, NaI, NaOH / H2O; toluene / 50 °C 2: 80 percent / NaBH(OAc)3, Et3N / CH2Cl2 / Ambient temperature 3: 68 percent / t-BuCO2H / 150 °C 4: 77 percent / EtONa / ethanol / Ambient temperature 5: 80 percent / NaH / tetrahydrofuran / Ambient temperature 6: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 7: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 8: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme