Water → HCID 178494609, compound

Participants

Reaction Conditions

Reaction Steps

Under N2, a mixture of NaH (1.5 g, 0.037 mol), 60% oil dispersion), DMF (45 mol) and 89 (6.8 g, 0.033 mol) was heated at 80° C. for 30 minutes and then a solution of 2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane methansulfonate (8.4 g, 0.04 mol) in DMF (25 ml) was added dropwise. After the addition, the mixture was heated at 120° C. with stirring for 18 hours. The mixture was then poured into H2O and the solution extracted with EtOAc (4×). The combined organic extracts were backwashed with H2O, 5% NaOH, dried, filtered and concentrated to dryness. The residue was combined with acetone (75 ml) and 3N HCl (75 ml) and the solution heated on a steam bath for 30 minutes. After cooling, the solution was adjusted to pH 10 and extracted with 10% CH3OH--CHCl3. The combined extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with 10% CH3OH--CHCl3 to yield 1.7 g of 90 (18%); m.p. 154°-56° C. (isoProOH).

Provenance & Evidence