Water → HCID 70006334, compound

Participants

Reaction Steps

To a solution of (62) (5 g) in Benzene (50 mL) p-TSA (500 mg) was added and the resulting mixture was heated at reflux for 6 hr. while water formed in the reaction was removed using a Dean-Stark Trap. The reaction mixture was allowed to cool down to room temperature and washed with water (5×50 mL). The organic layer was concentrated in vacuo to obtain an oil which was dried on a high vacuum and directly used in next step. To a solution of above product (4.8 g) in 1:1 t-BuOH/H2O (100 mL) was treated with NMO (3 g) and OsO4 (380 mg). The resulting mixture was stirred at RT for 12 hr. Aq. NaHCO3 (300 mL) and EtOAc (300 mL) were then added, and the product was extracted in to EtOAc. Organic phase was separated, and the concentrated in vacuo to obtain compounds (80) and (84) which were separated on silica (EtOAc:Hexane 2:3).

Provenance & Evidence