sodium periodate in methanol; water 10 h; Ambient temperature;

n-butyllithium in tetrahydrofuran 1.) -60 deg C, 15 min, 2.) -50 deg C, 1.5 h;

1: 1.) N-bromosuccinimide, benzoyl peroxide, 2.) sodium carbonate / 1.) carbon tetrachloride, reflux, 5 h, 2.) acetone, reflux, 5 h 2: 100 percent / sodium periodate / methanol; H2O / 10 h / Ambient temperature View Scheme

1: 1.) N-bromosuccinimide, benzoyl peroxide, 2.) sodium carbonate / 1.) carbon tetrachloride, reflux, 5 h, 2.) acetone, reflux, 5 h 2: 100 percent / sodium periodate / methanol; H2O / 10 h / Ambient temperature View Scheme