反応 #425724

反応方程式

acetic acid

4-bromobenzaldehyde

3-buten-1-ol

hydrobromic acid

→

title compound

収率 57.8%

4-bromo-2-(4-bromophenyl)tetrahydro-2H-pyran

収率 57.8%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他Reaction
2. 2
   その他was quenched by aqueous sodium bicarbonate
3. 3
   抽出extracted with ethyl acetate
4. 4
   洗浄washed with brine
5. 5
   乾燥dried over sodium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The residue was purified by silica gel chromatography

実験手順

To a solution of 4-bromobenzaldehyde (1.00 g, 5.41 mmol) and 3-buten-1-ol (800 mg, 10.8 mmol) in dichloromethane (20 mL) at room temperature was added zinc (II) bromide (25 mg, 0.11 mmol) followed by 33% hydrobromic acid (2.4 g) in acetic acid (4.9 g, 81 mmol) and stirred at room temperature for 5 hours. Reaction was quenched by aqueous sodium bicarbonate, then extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound (1.00 g) which contained some of 4-bromobenzaldehyde 1H NMR (400 MHz, CDCl3) δ ppm 7.49 (d, 2H) 7.24 (d, 2H) 5.19 (dd, 1H) 4.25 (m, 1H) 4.12 (m, 1H) 3.60 (m, 1H) 2.75 (m, 1H) 2.68 (m, 1H) 2.11 (m, 2H).

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