Allyl bromide → HCID 69890792, compound

Participants

Reaction Steps

Under a nitrogen stream, a solution of 0.76 g of 6-t-butyl-5-hydroxy-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane synthesized in Example 7 in 6 ml of dimethylformamide was added dropwise to a suspension of 0.13 g of oily sodium hydride in 6 ml of dimethylformamide at 0° C. After stirring for 30 minutes, 0.28 ml of allyl bromide was added dropwise and the mixture was stirred overnight and allowed to attain room temperature. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with n-hexane. 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 0.76 g of 6-t-butyl-5-(2-propenyloxy)-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane as a colorless oil (yield 90%).

Provenance & Evidence