Water → (1R)-1-[(2R)-6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-1,2-ethanediol

Participants

Reaction Conditions

Reaction Steps

(R)-6-fluoro-3,4-dihydro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene (2.92 g, 11.6 mmol) was dissolved in acetic acid (24 ml) and demi water (9 ml). The reaction mixture was stirred vigorously and heated to 65° C. After 3 h at 65° C. the reaction mixture was cooled to 25° C. The solution was then concentrated in vacuo to obtain a vetrous oil. Chromatographic separation on silica of the crude, using a mixture of heptane:ethyl acetate 1:1 as eluent, furnished 0.64 g of (R)-1-((R)-6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethane-1,2-diol as a white solid (26% yield).

Provenance & Evidence