Tetrabutylammonium Fluoride → Trans 2-(Diethyloxyphosphinoylmethyl)-5-(Hydroxymethyl)-1,3-Oxathiolane

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Reaction Steps

To a solution of cis and trans 5-(t-butyldiphenylsilyloxy methyl)-2-(diethyloxyphosphinoylmethyl)-1,3-oxathiolane (example 129) (15.68 g, 31.83 mmol) in THF (280 mL) was added tetrabutylammoniumfluoride (1 M solution in THF) (38.2 mL, 38.19 mmol, 1.2 eq.) at 0° C. The mixture was stirred at room temperature for 30 min. after which it was evaporated under reduced pressure. The residue was purified by flash chromatography with ethyl acetate:MeOH (95:5 to 93:7) to give 7.39 g of the compound in a 86% yield.

Provenance & Evidence