反応 #1104331

反応方程式

5-bromo-1-indanone

sodium borohydride

→

5-bromo-1-indanol

収率 100.0%

溶媒

ethanol

反応条件

後処理

1. 1
   その他A 2 L three-neck round bottom flask equipped with a condenser, mechanical stirrer, nitrogen inlet
2. 2
   温度The resulting suspension was warmed
3. 3
   その他the reaction
4. 4
   温度to reflux
5. 5
   温度Heating
6. 6
   温度to maintain
7. 7
   温度reflux for 14 hours
8. 8
   温度The reaction mixture was then cooled slightly
9. 9
   その他excess ethanol was removed by rotary evaporation, water (1 L) and diethyl ether (600 mL)
10. 10
    workup.ADDITIONwere added
11. 11
    その他The organic phase was separated
12. 12
    洗浄washed several times with water (6×500 mL)
13. 13
    乾燥dried over anhydrous magnesium sulfate
14. 14
    その他Evaporation of the diethyl ether

実験手順

A 2 L three-neck round bottom flask equipped with a condenser, mechanical stirrer, nitrogen inlet and a thermometer was charged with 5-bromo-1-indanone (Aldrich 98%, 50.0 g, 0.24 mol) and ethanol (700 mL). The resulting suspension was warmed, with stirring, to 40° C. and sodium borohydride (18.2 g, 0.48 mol) was added incrementally over 20 minutes. A moderate exotherm ensued which brought the reaction to reflux. Heating was applied to maintain reflux for 14 hours. The reaction mixture was then cooled slightly, excess ethanol was removed by rotary evaporation, water (1 L) and diethyl ether (600 mL) were added. The organic phase was separated, washed several times with water (6×500 mL), and dried over anhydrous magnesium sulfate. Evaporation of the diethyl ether gave a quantitative yield of 5-bromo-1-indanol (50.5 g, 0.24 mol) crystals. 1HNMR (CD2Cl2, 500 MHz) δ7.39 (s, 1H); 7.35 (dd, JAB=1, 8 Hz, 1H); 7.26 (d, JAB=8 Hz, 1H); 5.17 (br s, 1H); 3.00 (m, 1H); 2.80 (p, J=8 Hz, 1H); 2.46 (m, 1H); 1.92 (m, 1H); 1.86 (s, 1H).

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