反应 #5689

反应方程式

indole

4-chlorobenzyl chloride

KOH

→

1-(4-chlorobenzyl)indole

收率 84.1%

溶剂

H2O

toluene

H2O

反应条件

后处理

1. 1
   温度heated at 55°-65° for 22 hours
2. 2
   其他The layers were separated
3. 3
   萃取The aqueous layer was extracted with 100 mL of toluene
4. 4
   洗涤The combined organic phases were washed with 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine
5. 5
   干燥dried over MgSO4
6. 6
   其他Evaporation of the solvent
7. 7
   workup.WAITleft 29 g of orange-brown oil
8. 8
   其他The oil was chromatographed on a 1100 g column of silica gel
9. 9
   洗涤The column was eluted with 1:1 CH2Cl2 -Skellysolve B and 200 mL fractions
10. 10
    其他were collected
11. 11
    其他Fractions 12-19 were combined giving 23.11 g of crude product as a pink oil The oil
12. 12
    其他was chromatographed on a 1100 g column of silica gel
13. 13
    洗涤The column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions
14. 14
    其他were collected

实验过程

A mixture of 11.72 g (0.1 mole) of indole, 17.71 g (0.11 mole) of 4-chlorobenzyl chloride, 33 g (0.5 mole) of 85% KOH, 14 mL of H2O, 2.5 g (2.5 mmoles) of PEG-1000 and 100 mL of toluene was stirred and heated at 55°-65° for 22 hours. After cooling to room temperature, 50 mL of H2O was added. The layers were separated. The aqueous layer was extracted with 100 mL of toluene. The combined organic phases were washed with 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine and dried over MgSO4. Evaporation of the solvent left 29 g of orange-brown oil. The oil was chromatographed on a 1100 g column of silica gel. The column was eluted with 1:1 CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel tlc (1×4") (25% CH2Cl2 -Skellysolve B). Fractions 12-19 were combined giving 23.11 g of crude product as a pink oil The oil was chromatographed on a 1100 g column of silica gel. The column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed as before. Fractions 20-30 were combined giving 20.33 g (84%) of 1-(4-chlorobenzyl)indole as a yellow oil.

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