Multi-step reaction with 10 steps
1.1: potassium carbonate / ethanol / 1.5 h / Inert atmosphere; Reflux
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
3.2: 0.5 h / 0 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
5.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere
6.1: n-butyllithium / hexane; tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere; Molecular sieve
6.2: 0 °C / Inert atmosphere; Molecular sieve
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
8.1: methanesulfonyl chloride; triethylamine; lithium bromide / 0.08 h / 0 °C / Inert atmosphere; Reflux
8.2: 3 h / 0 - 20 °C / Inert atmosphere
8.3: Inert atmosphere
9.1: methanesulfonyl chloride; triethylamine; lithium bromide / 0.08 h / 0 °C / Inert atmosphere; Reflux
9.2: 3 h / 0 - 20 °C / Inert atmosphere
9.3: Inert atmosphere
10.1: sodium hydride; 15-crown-5 / tetrahydrofuran; mineral oil / 0.67 h / Inert atmosphere; Reflux
With
1H-imidazole; n-butyllithium; 15-crown-5; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; mineral oil;
8.1: |Arbuzov Reaction / 9.1: |Arbuzov Reaction / 10.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/jo4014244