反応 #1559938

反応方程式

2-(5-bromopentyl)-1,3-dioxolane

4-hydroxybenzaldehyde

potassium carbonate

→

title compound

収率 37.1%

4-((5-(1,3-Dioxolan-2-yl)pentyl)oxy)benzaldehyde

収率 37.1%

溶媒

dimethyl formamide

water

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate (×3)
2. 2
   洗浄The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine
3. 3
   乾燥dried (sodium sulfate)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他to afford an oil
7. 7
   その他The crude material was purified by silica gel column chromatography
8. 8
   洗浄eluting with 0-100% ethyl acetate in iso-hexane

実験手順

To a stirred solution of 2-(5-bromopentyl)-1,3-dioxolane (4.38 g, 19.6 mmol) in dimethyl formamide (30 mL) was added 4-hydroxybenzaldehyde (3.00 g, 24.4 mmol) and potassium carbonate (4.52 g, 32.8 mmol). The reaction mixture was stirred at 50° C. for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to afford an oil. The crude material was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (1.92 g, 36%).

出典