Sodium Methoxide → HCID 11344367, compound

HRID 2178267Notes

Reaction equation

HRID 2178267 reaction equation
C[O-].[Na+].C([O:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:17]([CH3:19])[CH3:18])[CH:12]=1)(=O)C>CO>[CH3:18][N:17]([CH3:19])[C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][CH2:9][CH2:8][OH:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59418776HCID 59418776, compound

Product 1

HCID 11344367HCID 11344367, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A catalytic amount of sodium methoxide (enough to insure a basic solution) was added to a solution of 2-(3-(dimethylamino)phenoxy)ethyl acetate (39A) (0.545 g, 2.44 mmol) in anhydrous MeOH (7 mL). The reaction mixture was stirred at rt for 2.5 hours before a small amount of acidic resin (Dowex 50WX8-200) was added. The reaction mixture was filtered, concentrated under reduced pressure and the crude material was purified by column chromatography on silica gel eluting with a gradient of PE:EtOAc 66:34-50:50, to provide the desired compound 2-(3-(dimethylamino)phenoxy)ethanol (39B).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customthe crude material was purified by column chromatography on silica gel eluting with a gradient of PE

Sources & evidence

ORD record
ord-19f22da4b7cd4fad94ad7666bd08fd1b
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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