Water → HCID 91618608, compound

Participants

Reaction Conditions

Reaction Steps

A solution of OsO4 in water (0.015 g/ml, 265 mL) was added into a 10-L 4-necked round-bottom flask with 2-chloro-4-ethenyl-5-fluoropyrimidine (303 g, 1.24 mol, 1.00 equiv, 65%), tetrahydrofuran (2400 mL) and water (1600 mL). This was followed by the addition of NaIO4(424 g, 1.94 mol, 1.56 equiv, 98%), in portions at 0-10° C. The resulting solution was stirred for 60 min at 0-10° C. in a water/ice bath. The resulting solution was diluted with water (4 L), then extracted with ethyl acetate (5×1000 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:5) to afford (2-chloro-5-fluoropyrimidin-4-yl)methanediol as a white solid and (2-chloro-5-fluoropyrimidin-4-yl)methanediol as a yellow oil.

Provenance & Evidence