Triacetoxyperiodinane → HCID 25008473, compound

Participants

Reaction Steps

Dess-Martin Periodinane (58.3 mg, 0.137 mmol) was added to a solution of alcohol from Example 51 (82 mg, 0.115 mmol) in methylene chloride (5 ml) at room temperature. The resulting slurry was stirred at room temperature for 1 h. No starting material was seen by TLC (EtOAc/hexane 2:8). The solid was filtered. The filtrate was concentrated. The residue was purified by flash column on silica gel, eluting with EtOAc/hexane (20:80) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz): δ a mixture of 1:1 atopoisomers 7.90 (s, 1H), 7.89 (s, 1H), 7.84 (d, J=8 Hz, 1H), 7.72 (m, 4H), 7.62 (d, J=8.5 Hz, 1H), 7.51 (d, J=8.0 Hz, 0.5H), 7.46 (d, J=8.0 Hz, 0.5H), 7.40-7.34 (m, 2H), 7.26 (d, J=2.5 Hz, 0.5H), 7.21 (d, J=2.5 Hz, 0.5H), 5.62 (d, J=8.0 Hz, 1H), 5.02 (d, J=15.5 Hz, 0.5H), 4.83 (d, J=16.0 Hz, 0.5H), 4.08 (d, J=16.0 Hz, 0.5H), 4.01 (d, J=15.5 Hz, 0.5H), 3.99 (m, 0.5H), 3.90 (m, 0.5H), 2.64 (s, 3H), 2.40 (s, 1.5M), 2.39 (s, 1.5H), 0.64 (d, J=6.5 Hz, 1.5H), 0.62 (d, J=6.5 Hz, 1.5H). LC/MS M+714.01.

Provenance & Evidence