Dimethyl Carbonate → HCID 86637074, compound

Participants

Reaction Conditions

Reaction Steps

Compound W (15.91 g, 46.7 mmol) was dissolved in THF (100 mL). NaH (55% in oil, 4.71 g, 98 mmol) was added portionwise, followed by dimethylcarbonate (8.86 mL, 105 mmol). The reaction mixture was heated to reflux for 1 h. The mixture was cooled to 0° C. with an ice bath, and treated cautiously with ice-water (50 mL). The org. layer was diluted with EtOAc (200 mL), and washed with aq. 1M HCl (100 mL), and with brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:3→1:2→1:1→2:1) yielded the title compound (Rf=0.7, EtOAc/heptane 1:1) as a yellow oil (10.96 g, 58%). LC-MS: tR=1.03, ES+: 399.25.

Provenance & Evidence