Ammonium Chloride → 5-Benzyloxy-4-t-butyl-2-(1-octenyl)benzofuran

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Reaction Steps

Under nitrogen atmosphere, 2.6 ml of n-butyl lithium (1.6 M in n-pentane) was added dropwise to a suspension of 1.84 g of n-heptylphenylphosphonium bromide in 10 ml of tetrahydrofuran. After stirring at room temperature for 30 minutes, a solution of 1.0 g of 5-benzyloxy-4-t-butyl-2-formylbenzofuran synthesized in Example 2-2) in 10 ml of tetrahydrofuran was added dropwise. Then, the mixture was heated under reflux for 30 minutes, cooled and then combined with a saturated aqueous ammonium chloride solution and extracted with chloroform. The organic layers were dried over anhydrous magnesium sulfate, then concentrated, and the residue was purified by silica gel column chromatography (in chloroform) to give 1.14 g of 5-benzyloxy-4-t-butyl-2-(1-octenyl)benzofuran as a colorless oil (yield 91%). 1H NMR (60 MHz, CDCl3) δ ppm: 0.89 (t, 3H, J=6.0 Hz), 1.13-1.72 (m, 8H), 1.56 (s, 9H), 1.93-2.62 (m, 2H), 5.03 (s, 2H), 6.02-6.40 (m, 2H), 6.78-7.46 (m, 8H).

Provenance & Evidence