2-Chloroethanol → HCID 66772437, compound

HRID 1644070Notes

Reaction equation

HRID 1644070 reaction equation
[CH2:1]([CH:3]([NH:6][C:7](=[O:17])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:4][CH3:5])[CH3:2].[OH-].[K+].Cl[CH2:21][CH2:22][OH:23]>C(O)C>[CH2:1]([CH:3]([NH:6][C:7](=[O:17])[CH:8]=[CH:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:21][CH2:22][OH:23])=[CH:14][CH:15]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 14797Potassium HydroxideHCID 66772886HCID 66772886, compound

Product 1

HCID 66772437HCID 66772437, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

N-(1-Ethyl-propyl)-3-(4-hydroxy-phenyl)-acrylamide (example 76a) (0.44 mmol, 103 mg) was dissolved in absolute ethanol with KOH (0.7 mmol, 37 mg). The mixture was stirred at 80° C. for 1 hr. Then 2-chloro-ethanol (1.76 mmol, 118 μL) was added dropwise and the mixture was refluxed overnight. Following evaporation the crude product was dissolved in dichloromethane and washed with water and 5% citric acid. The organic phase was evaporated and the residue was purified by chromatography on silica gel to give 73 mg of desired product (60%). 1H NMR (500 MHz, CDCl3): δ 0.92-0.95 (t, 6H), 1.25 (s, 1H), 1.40-1.46 (m, 2H), 1.59-1.64 (m, 2H), 3.93-3.94 (m, 1H), 3.95-3.98 (m, 2H), 4.09-4.11 (m, 2H), 5.28-5.30 (d, 1H), 6.26-6.29 (d, 1H), 6.88-6.90 (d, 2H), 7.43-7.45 (d, 2H), 7.56-7.59 (d, 1H). MS (M+H, 278.1).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customevaporation the crude product
  3. dissolutionwas dissolved in dichloromethane
  4. washwashed with water and 5% citric acid
  5. customThe organic phase was evaporated
  6. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-804a003afb444753945db231a96a4084
Source dataset
uspto-grants-2012_02
Patent number
US08124121B2

Reaction notes

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