반응 #79745

반응 방정식

ethyl bromoacetate

4-methoxyindole

n-butyl lithium

→

ethyl [4-methoxyindol-3-yl]acetate

용매

ethyl acetate

tetrahydrofuran

반응 조건

후처리

1. 1
   기타The cooling bath was removed
2. 2
   세척washed with water
3. 3
   세척washed with brine
4. 4
   건조dried over sodium sulfate
5. 5
   기타evaporated in vacuo
6. 6
   기타The residue was chromatographed on silica gel eluting with a gradient hexane/10-50% ethyl ether
7. 7
   기타to give

실험 절차

To a solution of 2.94 gm (20 mmol) of 4-methoxyindole in 150 ml of tetrahydrofuran was added slowly 13 ml of n-butyl lithium (1.6M in hexane; 20 mmol) followed by the slow addition of 20 ml of zinc chloride (1.0M in ethyl ether; 20 mmol) at 0-5° C. The cooling bath was removed and the solution stirred for 2 hours and then treated with 2.1 ml (25 mmol) of ethyl bromoacetate for 19 hours, diluted with ethyl acetate, washed with water, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a gradient hexane/10-50% ethyl ether to give starting material (40%) and then product, 2.3 gm, 50%, as an oil. 1H NMR (CDCl3) δ: 1.25 (t, 3H), 3.85 (s, 3H), 3.90 (s, 2H), 4.10 (q, 2H), 6.45 (d, 1H), 6.90 (d, 1H), 6.95 (s, 1H), 7.05 (t, 1H), 8.00 (br s, 1H).

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