Hydrochloric Acid → HCID 86706837, compound

Temperature

0 °C

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.

1. customresulting orange solution
2. temperatureThe reaction was cooled to −78° C.
3. temperaturethe resulting mixture was warmed to r.t.
4. stirringstirred for 1.30 h
5. customThereafter the reaction was quenched with water
6. extractionthe aqueous phase was extracted with dichloromethane
7. dry with materialthe collected organic layer dried over Na2SO4
8. customThe solvent was evaporated
9. customthe residue was purified by flash chromatography (hexane/AcOEt 50:1)
10. customto give the corresponding enolether as brownish oil
11. stirringthe resulting mixture was stirred at r.t. until consumption of the starting material
12. extractionthe aqueous phase was extracted with dichloromethane
13. dry with materialthe collected organic layers were dried over Na2SO4
14. customthe solvent evaporated

ORD record

ord-59519cc531904a899c3a62b7fa7be787

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09066938B2