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

HRID 2307920Notes

Reaction equation

HRID 2307920 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-fc3d2db505e24d9a93466fd8af65e9b3
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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