Toluene → HCID 22803368, compound

Participants

Reaction Steps

Under argon at -70°, 1.5 ml. of a 20% solution of diisobutylaluminum hydride was added to a solution, cooled to -60°, of 150 mg. of (1S,5R,6R,7R)-6-[(E)-3,3-ethylenedioxy-4-(2-naphthyloxy)-1-butenyl]-7-(tetrahydropyran-2-yloxy)-2-oxabicyclo[3,3,0]octan-3-one (prepared according to Example 5[b]) in 15 ml. of absolute toluene. After 30 minutes, the mixture was combined with 0.75 ml. of isopropanol and 0.75 ml. of water and agitated for 30 minutes at 0°, diluted with 150 ml. of methylene chloride, filtered off from the precipitated aluminum compound, and evaporated under vacuum, thus obtaining 146 mg. of the title compound as a colorless oil. IR: 3600, 1630, 1600, 970 cm-1.

Provenance & Evidence