Diiodomethane → HCID 86586194, compound

Participants

Reaction Steps

Under a nitrogen stream, 1.64 ml of diethylzinc (1M in n-hexane) was added dropwise into a solution of 0.18 ml of diiodomethane in 4 ml of anhydrous toluene at 0° C. Further to this solution was added dropwise 0.30 g of 6-t-butyl-5-hydroxy-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane synthesized in Example 7 and dissolved in 4 ml of anhydrous toluene. After stirring for 5 minutes, the solution was refluxed for 1.5 hours. The reaction solution was allowed to cool down, and then combined with a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate, and the organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 1%-2% ethyl acetate) to give 0.04 g of 6-t-butyl-5-hydroxy-4-methyl-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane (yield 13%) and 0.05 g of 6-t-butyl-4-ethyl-5-hydroxy-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane (yield 15%) both as white solids.

Provenance & Evidence