Multi-step reaction with 6 steps
1: 73 percent / EtONa / 1,2-dimethoxy-ethane / 48 h / Ambient temperature
2: 1.) NaH / 1.) ether, reflux, 2 h, 2.) ether, RT, overnight
3: 1.) copper(I) iodide, LiBr / 1.) ether, 0 deg C, 15 min, 2.) ether, -10 deg C, 12 h
4: 86 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature
5: 83 percent / LiCl, collidine, methanesulfonyl chloride / dimethylformamide / 5 h / 0 °C
6: 1.) NaH, 2.) NaI / 1.) THF, 3 h, 2.) THF, 12 h
With
2,3,5-trimethyl-pyridine; copper(l) iodide; lithium aluminium tetrahydride; sodium ethanolate; sodium hydride; methanesulfonyl chloride; sodium iodide; lithium chloride; lithium bromide;
In
1,2-dimethoxyethane; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo00275a048