Multi-step reaction with 6 steps
1: 93 percent / Ph3P, imidazole, iodine / diethyl ether; acetonitrile / 0.5 h / 25 °C
2: 1.) LDA, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 5 h; -78 to -20 deg C, 9 h
3: 90 percent / diisobutylaluminum hydride / CH2Cl2 / 2.5 h / -78 °C
4: 95 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / 0.5 h / -60 °C
5: 86 percent / LDA / tetrahydrofuran / 2 h / -78 °C
6: 72 percent / rhodium diacetate / 1,2-dimethoxy-ethane / 5 h / 25 °C
With
rhodium(II) acetate; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/ja00254a051