2-Methyl-2-butene → Ethyl N-(3,4-dichlorobenzyl)-2-ethoxycarbonylindole-3-carboxylate

HRID 2307920노트

반응식

HRID 2307920 반응식
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].[CH:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[C:14]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:12].CC(=[CH:39][CH3:40])C>O.C(O)(C)(C)C>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[Cl:29])[CH2:22][N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([C:11]([O:6][CH2:39][CH3:40])=[O:12])=[C:14]1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

참가 물질

7

반응물 4

HCID 105532-Methyl-2-buteneHCID 22603427Ethyl 3-formyl-N-(3,4-dichlorobenzyl)indole-2-carboxylateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

생성물 1

HCID 22603435Ethyl N-(3,4-dichlorobenzyl)-2-ethoxycarbonylindole-3-carboxylate수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

A mixture of sodium chlorite (3.39 g) and sodium dihydrogen orthophosphate (4.54 g) in water (50 ml) was added dropwise to a stirred solution of ethyl 3-formyl-N-(3,4-dichlorobenzyl)indole-2-carboxylate (1.56 g) and 2-methylbut-2-ene (50 ml) in tert-butyl alcohol (100 ml) at ambient temperature and reaction stirred vigorously overnight. The reaction mixture was concentrated in vacuo and the residue dissolved in dichloromethane (100 ml), washed with water (100 ml), dried (MgSO4) and concentrated in vacuo to give the product as a yellow solid (1.50 g, 92%); NMR d (CD3SOCD3) 1.20 (t, 3H), 4.30 (q, 2H), 5.50 (s, 2H), 7.00 (m, 1H), 7.25 (m, 2H), 7.42 (m, 1H), 7.58 (m, 2H), 8.00 (m, 1H), 12.68 (s, 1H); M/z (−) 390.4 (M−H+).

후처리

  1. customreaction
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in dichloromethane (100 ml)
  4. washwashed with water (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fc3d2db505e24d9a93466fd8af65e9b3
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06833387B1

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