Multi-step reaction with 10 steps
1.1: lithium hexamethyldisilazide / tetrahydrofuran
2.1: 6.60 g / tetrahydrofuran / 14 h / 22 °C
3.1: 98 percent / H2 / Pd/C / methanol; ethyl acetate / 22 °C / 1500.12 Torr
4.1: lithium diisopropylamide / tetrahydrofuran / 3 h / -50 °C
4.2: 96 percent / tetrahydrofuran / -78 - 20 °C
5.1: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 22 °C
6.1: sodium hydride / dimethylformamide / 1 h / 80 - 100 °C
6.2: 81 percent / dimethylformamide / 12 h / 22 °C
7.1: 83 percent / BF3*Et2O / CH2Cl2 / 5 h / 22 °C
8.1: 91 percent / sodium methoxide / methanol / 3 h / 22 °C
9.1: orthoperiodic acid / tetrahydrofuran / 1 h / 22 °C
9.2: 86 percent / lithium aluminum hydride / diethyl ether / 1 h / 22 °C
10.1: 85 percent / imidazole / dimethylformamide / 5 h / 22 °C
With
1H-imidazole; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; hydrogen; sodium methylate; sodium hydride; periodic acid; lithium hexamethyldisilazane; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200400653