Multi-step reaction with 5 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.33 h / 20 °C / Inert atmosphere; Cooling with ice
1.2: 1.17 h / 20 °C / Cooling with ice
2.1: calcium chloride; potassium borohydride / Tetraethylene glycol dimethyl ether; ethanol / 0.92 h / 20 - 35 °C / Cooling with ice
2.2: 1.17 h / 20 °C / Cooling with ice
3.1: tributylphosphine; diamide / tetrahydrofuran / 13 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / 1,3-bis-(diphenylphosphino)propane; palladium diacetate / N,N-dimethyl-formamide; -butyl vinyl ether / 20 h / 100 - 120 °C
4.2: 4 h / 20 °C
5.1: n-butyl(triphenyl)phosphonium bromide / hexane; tetrahydrofuran / 1 h / -78 - 20 °C
5.2: 16 h / 20 °C / Reflux
With
potassium borohydride; tributylphosphine; diamide; n-butyl(triphenyl)phosphonium bromide; sodium hydride; N-ethyl-N,N-diisopropylamine; calcium chloride;
1,3-bis-(diphenylphosphino)propane; palladium diacetate;
In
tetrahydrofuran; -butyl vinyl ether; ethanol; hexane; Tetraethylene glycol dimethyl ether; N,N-dimethyl-formamide; mineral oil;
3.1: Mitsunobu reaction;