Toluene → HCID 86591099, compound

Participants

Reaction Steps

A mixture of 20.0 mg (0.041 mmol) of 2-(3-chloro-2-fluoro-5-trifluoromethylbenzyl)-4-(2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol and 42.0 mg (0.185 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in 4 mL of toluene was warmed at reflux for 18 hours. The solvent was lost overnight and the oil bath temperature was 145° C. The residue was diluted with 10 mL of EtOAc and 1 N aqueous sodium hydroxide, treated with decolorizing carbon, and filtered through diatomaceous earth. The basic aqueous was separated and extracted with two 5 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of brine, three 5 mL portions of saturated aqueous ammonium chloride, two 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product which was purified by preparative TLC (2 mm, EtOAc-hexanes (1:9), silica gel) to afford 9.9 mg (50%) of the title compound as an oil.

Provenance & Evidence