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

HRID 2307920ノート

反応式

HRID 2307920 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-fc3d2db505e24d9a93466fd8af65e9b3
出典データセット
uspto-grants-2004_12
特許番号
US06833387B1

反応ノート

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