Nitrogen → HCID 53689240, compound

Participants

Reaction Conditions

Reaction Steps

2,2,6,6-Tetramethylpiperidine 1-oxyl (202 mg, 1.29 mmol) and (diacetoxyiodo)benzene (3.33 g, 10.4 mmol) were added to a solution of 8,8,8-trifluoro-octanol (˜8.63 mmol) in dichloromethane (34.5 mL) at 0° C. in an N2 atmosphere, and the mixture was stirred at 0° C. for five minutes and at room temperature for 1.5 hours. The reaction solution was diluted with dichloromethane (200 mL), and the organic layer was sequentially washed with a saturated aqueous sodium sulfite solution (100 mL), a saturated aqueous sodium bicarbonate solution (100 mL) and saturated brine (100 mL). The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 8,8,8-trifluoro-octanal as a colorless oily substance (310 mg, two steps, 20%).

Provenance & Evidence