Multi-step reaction with 9 steps
1.1: sodium hydride / tetrahydrofuran / 0.5 h / 23 °C
1.2: 13 / 6 h / 23 °C
2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C
2.2: 13; 17 / 1.5 h / -78 °C
3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / methanol; benzene / 2 h / 80 °C
4.1: hydrogen / palladium / benzene / 1 h / 760.05 Torr
5.1: N-Bromosuccinimide / tetrahydrofuran / 0.08 h
6.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C
6.2: 13; 17 / 1 h / -78 °C
7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / methanol; benzene / 72 h / 50 °C
8.1: pyridine hydrogenfluoride / tetrahydrofuran / 1.5 h / 0 °C
9.1: Dess-Martin periodane / dichloromethane / 0.33 h / 23 °C
With
N-Bromosuccinimide; hydrogen; tert.-butyl lithium; sodium hydride; sodium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride;
tetrakis(triphenylphosphine) palladium(0); palladium;
In
tetrahydrofuran; methanol; dichloromethane; pentane; benzene;
3.1: Suzuki coupling / 7.1: Suzuki coupling;
DOI:10.1021/ja027822b