Water → HCID 15545704, compound

HRID 1385903Notes

Reaction equation

HRID 1385903 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[OH:8])=[O:4].[OH-].[K+].O>C(O)C>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([CH:7]2[O:8][CH2:2][C:3](=[O:4])[NH:5][CH2:6]2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 21716316HCID 21716316, compound

Product 1

HCID 15545704HCID 15545704, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(2-chloroacetamido)-1-(3,4-dimethoxyphenyl)ethanol (3.30 g, 12.06 mM) and potassium hydroxide (2.98 g, 45.21 mM) in ethanol (300 ml) heated to reflux for one night. Water was added into the reaction solution, the solution was extracted with methylene chloride, the extract was dried over anhydrous sodium sulfate, then the solvent was evaporated in vacuo to obtain a crude product as a brown solid. The crude product was purified by flash chromatography (SiO2; eluted by gradient of range from ethyl acetate to 4% methanol/ethyl acetate), to obtain the above-described compound 1.47 g (yield 51.4%) as a light yellow solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for one night
  3. extractionthe solution was extracted with methylene chloride
  4. dry with materialthe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customto obtain a crude product as a brown solid
  7. customThe crude product was purified by flash chromatography (SiO2; eluted by gradient of range from ethyl acetate to 4% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-ef62a358bc1445f59c64d2b8f9ef2765
Source dataset
uspto-grants-2001_07
Patent number
US06265402B1

Reaction notes

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