Nitrogen → HCID 86660666, compound

Participants

Reaction Conditions

Reaction Steps

2,2,6,6-Tetramethylpiperidine 1-oxyl (309 mg, 1.98 mmol) and (diacetoxyiodo)benzene (7.01 g, 21.8 mmol) were added to a solution of 4-hydroxymethyl-cyclohexanecarboxylic acid benzyl ester (cis-trans=4:1 mixture) (4.91 g, 19.8 mmol) at 0° C. in an N2 atmosphere, and the mixture was stirred at 0° C. for one hour and at room temperature for seven 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 4-formyl-cyclohexanecarboxylic acid benzyl ester (cis-trans=4:1 mixture) as a colorless oily substance (4.44 g, 91%).

Provenance & Evidence