Multi-step reaction with 8 steps
1: 1.) NEt3, 2.) NaH / 1.) THF, 0 deg C to r.t., 12 h, 2.) r.t., 1-2 weeks
2: BuLi / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 2.) -78 deg C to r.t., 12 h
3: BF3*OEt2 / methanol; CH2Cl2 / 12 h / Ambient temperature
4: pyridine / CH2Cl2 / 12 h / Ambient temperature
5: 1.) THF, Me2N(CH2)2NMe2, -78 deg C, 40 min, 2.) -78 deg C to r.t., 12 h
6: 89 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.02 h / Ambient temperature
7: 79 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 12 h / Ambient temperature
8: DIBAL-H / CH2Cl2 / 2 h / -78 - 20 °C
With
pyridine; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1039/a706333d