Tetrapropylammonium → HCID 18922186, compound

Participants

Reaction Steps

To 1.0 g (3.5 mmol) of a stirring solution of 5-bromo-2,3-dihydro-3,3-dimethylbenzo[b]furan in 2.0 mL of ether and 18 mL of dry hexane at -78° C. is added 4.4 mL (7.1 mmol) of t-butyllithium in hexane. The resulting mixture is stirred for 40 min., then 0.5 g (4.6 mmol) of 2-pyridinecarboxaldehyde is added. The reaction is allowed to slowly reach RT and is then quenched with water. The reaction is then diluted with 50 mL of ether, and the organic layer is separated. The remaining aqueous layer is extracted with ether (3×20 mL). The organic layers are then combined, dried over MgSO4, filtered, and the solvent was removed in vacuo. The residue is dissolved in 20 mL CH2Cl2, and to this solution was added 0.1 g (0.4 mmol) of tetrapropylammonium perruthinate followed by 0.6 g (5.3 mmol) of N-methyl morpholine-N-oxide at RT. The reaction is stirred for 3 h, then filtered through silica gel, and the solvent is removed in vacuo. Purification by sgc with 1 ethyl acetate : 5 hexane resultes in about 0.30 g (29%) of a yellow solid. mp 95°-97° C.

Provenance & Evidence