Diethyl Ether → HCID 54208735, compound

Participants

Reaction Steps

11-Benzyloxy-6,10-dimethyl-2-trimethylsiloxy-undec-1,5-diene (15.36 g, 41 mM) in dry tetrahydrofuran (400 ml) is treated with sodium bicarbonate (4.1 g, 49 mM) and N-bromosuccinimide (7.3 g, 41 mM) at -70° C. and allowed to stir for 4 hours. The reaction mixture is allowed to reach room temperature after which saturated sodium bicarbonate, ether and brine are added. The phases are separated, the aqueous phase is extracted with ether and the combined organic extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give crude 11-benzyloxy-1-bromo-6,10-dimethyl-2-oxo-undec-5-ene (17 g).

Provenance & Evidence