2-Methyl-2-butene → HCID 11257842, compound

HRID 1166053Notes

Reaction equation

HRID 1166053 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].[CH:11]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:17]2[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)=[O:12].CC(=CC)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:17]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:13]([C:11]([OH:6])=[O:12])[C:14]=2[CH:15]=[C:16]1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 22997273HCID 22997273, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 11257842HCID 11257842, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of sodium chlorite (9.70 g) and sodium dihydrogen orthophosphate (13.02 g) in water (50 ml) was added dropwise to a solution of ethyl 4-formyl-N-(3,4-dichlorobenzyl)indole-2-carboxylate (4.47 g) and 2-methylbut-2-ene (50 ml) in tert-butyl alcohol (100 ml) and the mixture stirred for 72 hours at ambient temperature, then concentrated in vacuo and the resulting precipitate was filtered and dried to give the product as an off-white solid (4.16 g. 89%); NMR δ(CD3SOCD3) 1.25 (t, 3H), 4.30 (q, 2H)) 5.85 (s, 2H), 6.85 (m, 1H), 7.35 (m, 1H), 7.40 (q, 1H), 7.50 (m, 1H), 7.80 (m, 3H); M/z (−) 390.1 (M−H+).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationthe resulting precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-b79a59ca5c7e435f8bb36b4a71f129dd
Source dataset
uspto-grants-2003_09
Patent number
US06613760B1

Reaction notes

Loading…