Multi-step reaction with 7 steps
1: 1) n-BuLi / 1) THF, -76 deg C, 10 min, 2) THF, 1 h
2: 90 percent / diisopropylethyl amine / CH2Cl2 / 3.5 h / 23 °C
3: 92 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
4: 97 percent / pyridine / a) 0 deg C, 15 min, b) 20 min
5: 98 percent / (n-Bu)4NF / tetrahydrofuran / 0.33 h / 23 °C
6: 87 percent / NaH / tetrahydrofuran / 2.5 h
7: 1) NaH, n-BuLi / 1) THF, 0 deg C, 10 min, 2) THF, 0 deg C, 1 h
With
pyridine; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00008a049