1-Iodohexane → Ethyl 2-Hexylhexan-3-onecarboxylate

Reaction equation

[Na].[CH2:2]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3][C:4](=[O:8])[CH2:5][CH2:6][CH3:7].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)C>[CH2:15]([CH:3]([C:4](=[O:8])[CH2:5][CH2:6][CH3:7])[CH2:2][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Procedure

Under an atmosphere of argon, 1.59 g (69.3 mmol) of sodium were added a little at a time to 50 ml of ethanol. The mixture was then stirred under reflux until a homogeneous solution was obtained. 11.0 g (69.3 mmol) of ethyl hexan-3-onecarboxylate were added to the hot alkoxide solution, and the mixture was stirred for 45 min. 6.51 ml (7.93 g, 52.5 mmol) of 1-iodohexane were then slowly added dropwise to the boiling mixture. The mixture was stirred under reflux for 16 h, cooled to room temperature and filtered, and the solvent was then removed under reduced pressure. The residue was taken up in dichloromethane, filtered again and concentrated. The crude product was purified chromatographically (silica gel, petroleum ether: ethyl acetate 30:1). MS (DCI, NH3): 309 [M+H]+.