Trimethyl orthoformate → HCID 20305770, compound

Participants

Reaction Steps

7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)-6-methyl-heptan-2-ol (16.9 g, 41 mM) is treated with distilled trimethylorthoformate (51 ml, 66 mM) and 0.1 N sulfuric acid/methanol (15.3 ml) at 0° C. for 0.5 hours and then at 5° C. for 66 hours. The solvent is removed in vacuo and the residue obtained is treated with ether, saturated sodium bicarbonate and brine. The layers are separated, the aqueous phase is extracted with ether and the combined ether extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give crude 7-benzyloxy-2-[2-bromomethyl-2-methoxy-tetrahydrofuran-5-yl]-6-methyl-heptan-2-ol.

Provenance & Evidence