Water → 11-Hydroxy-2-(2-triphenylmethyloxyethyl)-6,11-dihydrodibenz[b,e]oxepin

HRID 1196990Notes

Reaction equation

HRID 1196990 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH:22][CH:23]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH2:27][O:26][C:25]2[CH:34]=[CH:35][C:36]([CH2:38][CH2:39][OH:40])=[CH:37][C:24]1=2>N1C=CC=CC=1>[OH:22][CH:23]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH2:27][O:26][C:25]2[CH:34]=[CH:35][C:36]([CH2:38][CH2:39][O:40][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:37][C:24]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 6456Trityl chlorideHCID 12330037HCID 12330037, compound

Product 1

HCID 1574939911-Hydroxy-2-(2-triphenylmethyloxyethyl)-6,11-dihydrodibenz[b,e]oxepinYield 64.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

In this process, 17.2 g of 11-hydroxy-2-(2-hydroxyethyl)-6,11-dihydrodibenz[b,e]oxepin is dissolved in 50 ml of pyridine. To the solution is added 30 g of triphenylchloromethane and the mixture is stirred at 50° C. for 5 hours. After adding water and stirring the mixture for 2 hours, the solvent is distilled away under reduced pressure. The mixture is extracted with 1000 ml of ethyl acetate, washed with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent is distilled away under reduced pressure and the resultant residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate=3:1 ) to obtain 21.7 g of the desired product as a colorless amorphous.

Workup

  1. stirringstirring the mixture for 2 hours
  2. distillationthe solvent is distilled away under reduced pressure
  3. extractionThe mixture is extracted with 1000 ml of ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is distilled away under reduced pressure
  7. customthe resultant residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate=3:1 )

Sources & evidence

ORD record
ord-d5b188665b194c75ae6f4d6c91dab5d8
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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