Tetrahydrofuran → HCID 59444766, compound

Participants

Reaction Steps

Potassium tert-butoxide (38.2 mg, 0.341 mmol) was added to an anhydrous THF (3 ml) solution of methyltriphenylphosphonium iodide (100 mg, 0.247 mmol) at room temperature, and it was stirred at room temperature for 30 minutes. Subsequently, a THF (3 ml) solution of (3aS,4E,6S,7S,13aR)-11-{[tert-butyl(dimethyl)silyl]oxy}-7-[(E)-2-formyl-1-methyletha-1-en-1-yl]-6,13a-dimethyl-2-phenyl-3a,6,7,10,11,12,13,13a-octahydro-9H-[1,3]dioxolo[4,5-f]oxacyclododecin-9-one (150 mg, 0.284 mmol) was added dropwise to this reaction solution at room temperature and the reaction solution was stirred for one hour. The reaction solution was diluted with ethyl acetate and washed with distilled water and brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto, commercial name Silica Gel 60N, 40-100 μm; heptane:ethyl acetate=20:1) to obtain the title compound (44 mg) as a white solid. The title compound was determined to be a mixture of α benzylidene acetal and β benzylidene acetal in a ratio of 1:3.2 by 1H-NMR.

Provenance & Evidence