Dimethylformamide → 6-Ethoxy-2,5,7,8-tetramethyl-2-(4-nitrophenoxymethyl)chroman

HRID 1030430Notes

Reaction equation

HRID 1030430 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:5]([CH3:28])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH3:27])([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[CH2:8][CH2:7]2.CN(C)C=O.[CH2:34](I)[CH3:35]>O.C1C=CC=CC=1>[CH2:34]([O:3][C:4]1[C:5]([CH3:28])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH3:27])([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[CH2:8][CH2:7]2)[CH3:35]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 134888696-Hydroxy-2,5,7,8-tetramethyl-2-(4-nitrophenoxymethyl)chroman

Product 1

HCID 198221956-Ethoxy-2,5,7,8-tetramethyl-2-(4-nitrophenoxymethyl)chroman

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

1.6 g of a 55% w/w suspension of sodium hydride in mineral oil was added to a mixture of 11 g of 6-hydroxy-2,5,7,8-tetramethyl-2-(4-nitrophenoxymethyl)chroman and 100 ml of dimethylformamide, and the reaction mixture was stirred for 1 hour at room temperature. Then a mixture of 5.7 g of ethyl iodide and 5 ml of benzene was added dropwise, whilst ice-cooling, and the reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was then poured into water and extracted with benzene. This extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled from the extract under reduced pressure, and the residue was purified by silica gel column chromatography eluted with a 3:7 by volume mixture of cyclohexane and benzene, to give the title compound.

Workup

  1. additionwas added dropwise, whilst ice-
  2. temperaturecooling
  3. stirringthe reaction mixture was stirred for 2 hours at room temperature
  4. extractionextracted with benzene
  5. washThis extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled from the
  8. extractionextract under reduced pressure
  9. customthe residue was purified by silica gel column chromatography
  10. washeluted with a 3:7 by volume mixture of cyclohexane and benzene

Sources & evidence

ORD record
ord-d9c72a3d8deb4c689e8213fe6637da30
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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