Acetonitrile--water (1/1) → HCID 86750303, compound

Participants

Reaction Steps

LiAlH4 (15.2 mg, 0.40 mmol) was added to a solution of tris(8-ethoxycarbonylmethylthio-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methanol (10.5 mg 0.10 mmol (Example 27)) in diethyl ether (10 mL) under nitrogen at 20° C. The reaction was followed by HPLC (reversed phase C18, acetonitrile:water (3:1), 5 mM tetrabutylammonium acetate). The mixture was quenched with ethylacetate when no more substrate was seen by HPLC. Dilute sulfuric acid was then added until pH 6-7. The ether phase was separated, and the water phase was extracted with diethyl ether. The combined etheric phases were dried (MgSO4) and evaporated, yielding 0.0901 g (97.8%, 0.0978 mmol) of a yellowish oil, which gradually crystallized upon standing.

Provenance & Evidence