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(R)-(-)-1 3-NONANEDIOL 97 synthesis

5synthesis methods
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Yield:1117-86-8 32% ,23433-07-0 10% ,18755-31-2 32%

Reaction Conditions:

Stage #1: chlorobromomethane;2,2'-(octane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)with n-butyllithium in diethyl ether at -78 - 20; for 0.0221667 h;Schlenk technique;Inert atmosphere;Matteson Homologation;
Stage #2: with 2,6-di-tert-butyl-4-methyl-phenol;dihydrogen peroxide;sodium hydroxide in tetrahydrofuran;diethyl ether at 0 - 20; for 1 h;Schlenk technique;Inert atmosphere;regioselective reaction;Matteson Homologation;

References:

Fawcett, Alexander;Nitsch, Dominik;Ali, Muhammad;Bateman, Joseph M.;Myers, Eddie L.;Aggarwal, Varinder K. [Angewandte Chemie - International Edition,2016,vol. 55,# 47,p. 14663 - 14667][Angew. Chem.,2016,vol. 128,# 47,p. 14883 - 14887] Location in patent:supporting information