반응 #2395098

반응 방정식

3,4-Dichlorobenzyl chloride

methyl 2-methoxycarbonyl-3-indoleacetate

potassium carbonate

→

product

수율 65.1%

Methyl N-(3,4-dichlorobenzyl)-2-methoxycarbonyl-3-indoleacetate

수율 65.1%

용매

acetonitrile

반응 조건

후처리

1. 1
   농축The reaction was concentrated in vacuo
2. 2
   기타partitioned between ethyl acetate and water
3. 3
   세척Combined organic extracts were washed with saturated aqueous sodium chloride solution
4. 4
   건조dried (MgSO4)
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by column chromatography

실험 절차

3,4-Dichlorobenzyl chloride (8.2 g) was added to a stirred solution of methyl 2-methoxycarbonyl-3-indoleacetate (6.5 g) and potassium carbonate (8.36 g) in acetonitrile (200 ml) under an atmosphere of argon. The reaction was heated to 80° C. for 24 hours. The reaction was concentrated in vacuo and partitioned between ethyl acetate and water. Combined organic extracts were washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using 25% ethyl acetate:iso-hexane as eluent to give the product as a white solid (6.95 g, 65%), NMR d (CD3SOCD3) 3.60 (s, 3H), 3.77 (s, 3H), 4.13 (s, 2H), 5.89 (s, 2H), 6.89 (dd, 1H), 7.16 (t, 1H), 7.27 (d, 1H), 7.34 (t, 1H), 7.52 (d, 1H), 7.57 (d, 1H), 7.78 (d, 1H); M/z (+) 406 (MH+).

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