Benzene → HCID 19822258, compound

HRID 1030377Notes

Reaction equation

HRID 1030377 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:40]=[CH:39][C:12]([O:13][CH2:14][C:15]3([CH3:38])[CH2:24][CH:23](O)[C:22]4[C:17](=[C:18]([CH3:37])[C:19]([CH3:36])=[C:20]([O:27][CH2:28][C:29]([O:31][CH2:32]COC)=[O:30])[C:21]=4[CH3:26])[O:16]3)=[CH:11][CH:10]=2)[S:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O1CCOCC1>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]3([CH3:38])[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([CH3:37])[C:19]([CH3:36])=[C:20]([O:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:21]=4[CH3:26])[O:16]3)=[CH:39][CH:40]=2)[S:3]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 19822206HCID 19822206, compound

Product 1

HCID 19822258HCID 19822258, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 970 mg of 2-methoxyethyl α-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]4-hydroxy-2,5,7,8-tetramethylchroman-6-yloxy}acetate (prepared as described in Example 37), 50 mg of p-toluenesulfonic acid, 10 ml of benzene and 1 ml of dioxane was heated under reflux in a nitrogen stream for 60 minutes. The reaction mixture was then washed with a 5% w/v aqueous solution of sodium bicarbonate and then with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluted with a 7:3 by volume mixture of benzene and ethyl acetate), to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a nitrogen stream for 60 minutes
  3. washThe reaction mixture was then washed with a 5% w/v aqueous solution of sodium bicarbonate
  4. dry with materialwith water, and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (
  7. washeluted with a 7:3 by volume mixture of benzene and ethyl acetate),

Sources & evidence

ORD record
ord-b2215a693cad431ba61dfbd95fcc80ab
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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