反应详情

A stirred solution of verbenone (about 10 g, 66.57 mmol) in CCl4: ACN: H2O (140 ml) NaIO4 (56.9 g, 266.3 mmol) followed by RuCl3.H2O (catalytic) were added at 0° C. and allowed to stir at room temperature for about 12 hours. After completion of the reaction (monitored by TLC), reaction mixture was diluted with EtOAc (about 200 ml), filtered through celite bed and the organic layer was separated, the aqueous layer extracted with EtOAc (100 ml×2) combined the organic layers dried with Na2SO4 and concentrated under reduced pressure. The resulting crude was stirred in hexane. Solid was filtered and dried under vacuum (8.56 g). 1H NMR (300 MHZ, CDCl3): δ 2.91-2.77 (m, 2H), 2.63 (q, 1H, J=9 Hz), 2.07 (s, 3H), 1.86-1.95 (m, 1H), 1.40 (s, 3H), 0.97 (s, 3H). Mass: [M+1]+ 171 (10%), [M+Na]+ 193 (72%). IR (KBr, cm−1): 3218, 1737, 1694, 1467, 1368, 1283, 1174, 1080, 836, 703. M.R: 109.5° C.-120.7° C.

1. additionwere added at 0° C.
2. customAfter completion of the reaction (monitored by TLC), reaction mixture
3. filtrationfiltered through celite bed
4. customthe organic layer was separated
5. extractionthe aqueous layer extracted with EtOAc (100 ml×2)
6. dry with materialdried with Na2SO4
7. concentrationconcentrated under reduced pressure
8. stirringThe resulting crude was stirred in hexane
9. filtrationSolid was filtered
10. customdried under vacuum (8.56 g)
11. custom109.5° C.-120.7° C.