Imidazole → HCID 54686174, compound

Participants

Reaction Steps

4-Hydroxy-6-hydroxymethylpyran-2-one (14.6 parts) was dissolved in dimethyl formamide (30 parts) at 20° C., imidazole (17.2 parts) was added and the temperature of the mixture cooled to 13° C. t-Butyldimethylsilyl chloride (17.1 parts) was then added in portions, the temperature was allowed to rise to 25° C. and maintained at 25°-30° C. by external cooling. The mixture was stirred for a further hour at 25°-30° C., before pouring into water (1100 parts) and stirring for 30 minutes until the product crystallised. The product was filtered off, washed with water (2×200 parts) and dried at 40° C./20 mm to give 6-t-butyldimethylsilyloxymethyl-4-hydroxy pyran-2-one (12.1 parts, 47%) m.pt 139°-141° C. Extraction of the filtrates with dichlorometane gave a further 7.0 parts, 27% of the product.

Provenance & Evidence