Ethylene Glycol → 5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1-(4-nitrobenzyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 342805Notes

Reaction equation

HRID 342805 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16](=[O:18])[CH3:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[CH2:29](O)[CH2:30][OH:31].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16]1([CH3:17])[O:31][CH2:30][CH2:29][O:18]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 544815121-(4-Nitro-benzyl)-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Ethyl Ester

Product 1

HCID 675989085-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1-(4-nitrobenzyl)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-nitro-benzyl)-5-(2-oxo-propyl)-1H-indole-2-carboxylic acid ethyl ester (1.91 g, 5.03 mmol), ethylene glycol (406 mg, 0.365 ml, 6.54 mmol), and p-toluenesulfonic acid monohydrate (110 mg, 0.58 mmol) in toluene (50 ml) was heated to about 150° C. under a Dean-Stark trap under nitrogen for two hours. The solution was cooled, diluted with ethyl acetate, washed with dilute sodium bicarbonate and brine, dried over sodium sulfate, filtered, and dried under reduced pressure to give the title compound in crude form (2.4 g), which was reacted without further purification.

Workup

  1. temperatureThe solution was cooled
  2. washwashed with dilute sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd35d2113b5547fc91511540aa802b32
Source dataset
uspto-grants-1999_01
Patent number
US05859044

Reaction notes

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