Triacetoxyperiodinane → HCID 86700850, compound
Reaction equation
[Br:1][CH:2]1[C:7]2([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[CH2:8][CH2:9][C:4]([CH2:17][OH:18])([CH2:5][O:6]2)[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][CH:2]1[C:7]2([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[CH2:8][CH2:9][C:4]([CH:17]=[O:18])([CH2:5][O:6]2)[CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of [6-bromo-1-(4-chloro-phenyl)-2-oxa-bicyclo[2.2.2]oct-4-yl]-methanol (2.47 g, 7.45 mmol) in dichloromethane (100 ml) at −78° C., was added Dess-Martin periodinane (3.32 g, 7.82 mmol). The reaction mixture was allowed to warm to 0° C. for 30 minutes and then room temperature for 60 minutes. Most of the solvent was removed by evaporation under vacuum at the room temperature and the residue was purified by flash chromatography (heptanes/acetone 1/2) to afford 6-bromo-1-(4-chloro-phenyl)-2-oxa-bicyclo[2.2.2]octane-4-carbaldehyde (2.0 g, 81%) as colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.98-2.21 (m, 3H) 2.34-2.44 (m, 1H) 2.69-2.80 (m, 1H) 2.82-2.92 (m, 1H) 3.92-4.08 (m, 2H) 4.21-4.32 (m, 1H) 7.25 (d, J=8.60 Hz, 2H) 7.34 (d, J=8.60 Hz, 2H) 9.44 (s, 1H).