Multi-step reaction with 8 steps
1: 82 percent / potassium carbonate / CH2Cl2; H2O / 1.) 0 deg C, 2 h, 2.) RT, 14 h
2: 83 percent / potassium tert-butoxide / tetrahydrofuran / 2 h / Heating
3: 54 percent / 2,4,6-trimethylpyridine, LiCl / dimethylformamide / 1.) 0 deg C, 15 min, 2.) 25 deg C, 3 h
4: 81 percent / 1,1,1,3,3,3-hexamethyldisilazane, n-butyllithium / tetrahydrofuran / 2 h
5: 46 percent / n-butyllithium / tetrahydrofuran / 0.83 h / -78 °C
6: 88 percent / 2,6-lutidine / CH2Cl2 / 30 h / 25 °C
7: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, methanol, RT, 5 h
8: 1.) triethylamine, methanesulfonyl chloride, 2.) NaBH4 / 1.) THF, 0 deg C, 1 h, 2.) ethanol, 65 deg C, 1 h
With
2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; n-butyllithium; potassium tert-butylate; potassium carbonate; ozone; methanesulfonyl chloride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium chloride;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;