反応 #2286322
ord-3167aac71b6b483d94b0756a6caffe80
反応方程式
反応物
反応条件
後処理
- 1抽出This mixture was extracted with methylene chloride (3×50 mL)
- 2洗浄washed with a saturated aqueous sodium chloride solution (30 mL)
- 3乾燥dried with magnesium sulfate
- 4ろ過filtered
- 5濃縮concentrated under vacuum
- 6その他The resulting oil was purified by flash chromatography (Isco 120 g column)
- 7洗浄eluted with 15% ethyl acetate in hexanes
- 8その他The desired fractions were collected
- 9濃縮concentrated under vacuum
- 10その他to afford an oil which
- 11その他was dried under high vacuum
実験手順
A solution of 2,6-dibromo-4-hydroxymethyl-phenyl)-acetonitrile (59) (1.4 g, 4.59 mmol) in methylene chloride (30 mL) at room temperature was treated with 3,4-dihydro-2H-pyran (0.46 mL, 5.04 mmol) and p-toluenesulfonic acid monohydrate (16.10 mg, 0.085 mmol). The reaction mixture was stirred for 45 min and was then treated with a saturated aqueous sodium bicarbonate solution (3 mL), a saturated aqueous sodium chloride solution (10 mL) and water (10 mL). This mixture was extracted with methylene chloride (3×50 mL). The organic layers were combined and washed with a saturated aqueous sodium chloride solution (30 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting oil was purified by flash chromatography (Isco 120 g column) using silica gel eluted with 15% ethyl acetate in hexanes. The desired fractions were collected and concentrated under vacuum to afford an oil which was dried under high vacuum to afford of [2,6-dibromo-4-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-acetonitrile (60) as a pale yellow oil (1.52 g, 85.4%). Used without further purification. Molecular Weight=389.0892; Exact Mass=386.9470