Hydrochloric Acid → HCID 86706837, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methoxymethyltriphenylphosphonium chloride (1.0 eq.) in dry THF cooled to 0° C., NaHMDS (1 M solution in THF, 1.0 eq.) was added, and resulting orange solution was stirred at 0° C. for 30 min. The reaction was cooled to −78° C. and a solution of 5-(benzyloxy)-2-bromobenzaldehyde (1.0 eq.) in THF was added dropwise, and the resulting mixture was warmed to r.t. and stirred for 1.30 h. Thereafter the reaction was quenched with water and the aqueous phase was extracted with dichloromethane and the collected organic layer dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography (hexane/AcOEt 50:1) to give the corresponding enolether as brownish oil; 6 N hydrochloric acid was added dropwise to a solution of the above compound in acetone and the resulting mixture was stirred at r.t. until consumption of the starting material. Thereafter water was added and the aqueous phase was extracted with dichloromethane, the collected organic layers were dried over Na2SO4, and the solvent evaporated to give the crude 2-[5-(benzyloxy)-2-bromobenzyl]-1,3-dioxolane as a yellowish oil which was immediately used for the next reaction.

Provenance & Evidence