Multi-step reaction with 6 steps
1: 69 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, hexane, -60 deg C, 1 h, 2.) THF, hexane, from -60 deg C to 0 deg C, 2 h
3: 1.) CuI / 1.) ether, 0 deg C, 45 min, 2.) ether, from -90 deg C to -85 deg C, 3 h
4: DIBAL / toluene / 3 h / -78 - -35 °C
5: 69 percent / LiCl, 2,4,6-trimethylpyridine, methanesulfonyl chloride / acetonitrile / 4 h / 0 °C
6: 1.) n-BuLi, t-BuONa / 1.) hexane, THF, -78 deg C, 1 h, 2.) hexane, THF, from -85 deg C to -55 deg C, 1 h
With
2,4,6-trimethyl-pyridine; copper(l) iodide; n-butyllithium; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; lithium chloride; sodium t-butanolate;
In
dichloromethane; toluene; acetonitrile;
DOI:10.1246/bcsj.66.3464