alpha-Hydroxyacetophenone → HCID 599077, compound

Participants

Reaction Steps

2-Hydroxyacetophenone (220 mmol, 30 g) is stirred in a mixture of dimethylformamide-dimethyl acetal for 5 hours at 70° C., cooled and recrystallised from diethylether. The intermediate is dissolved in dry ethanol (200 ml) and formamidine acetate (0.61 mmol, 63.5 g) is added. A solution of sodium (0.61 mol, 14 g) in ethanol (450 ml) is added in several portions and the mixture is refluxed for 18 hours and evaporated. Recrystallisation from diisopropylether yielded 3.6 g (10%) of 2-(pyrimidin-4-yl)phenol as a solid. This phenolic product is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to yield the title epoxide.

Provenance & Evidence