Multi-step reaction with 19 steps
1.1: sodium hydride; 15-crown-5 / tetrahydrofuran; mineral oil / 0 °C
1.2: -40 - 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
3.1: phosphorus tribromide / diethyl ether / 0 °C / Inert atmosphere
4.1: sodium ethanolate / ethanol / 0 °C
4.2: 16 h / 0 - 20 °C
5.1: potassium hydroxide / methanol; water / 2 h / 80 - 85 °C
6.1: sodium hydride; 15-crown-5 / tetrahydrofuran; mineral oil / 0 °C
6.2: -40 - 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
8.1: phosphorus tribromide / diethyl ether / 0 °C / Inert atmosphere
9.1: sodium ethanolate / ethanol / 0 °C / Inert atmosphere
9.2: 16 h / 0 - 20 °C
10.1: potassium hydroxide / methanol; water / 2 h / 80 - 85 °C
11.1: sodium hydride; 15-crown-5 / tetrahydrofuran; mineral oil / 0.25 h / 0 °C
11.2: -40 - 20 °C
12.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
13.1: phosphorus tribromide / diethyl ether / 0 °C / Inert atmosphere
14.1: sodium ethanolate / ethanol / 0 °C
14.2: 16 h / 0 - 20 °C
15.1: potassium hydroxide / methanol; water / 2 h / 80 - 85 °C
16.1: sodium hydride; 15-crown-5 / tetrahydrofuran; mineral oil / 0 °C
16.2: -40 - 20 °C
17.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
18.1: phosphorus tribromide / diethyl ether / 0 °C / Inert atmosphere
19.1: sodium ethanolate / ethanol / 0 °C
19.2: 16 h / 0 - 20 °C
With
lithium aluminium tetrahydride; 15-crown-5; sodium ethanolate; phosphorus tribromide; sodium hydride; potassium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; water; mineral oil;