2-Chloroethanol → HCID 86708302, compound

HRID 402616Notes

Reaction equation

HRID 402616 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][CH2:11][C:12](=[O:19])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl[CH2:21][CH2:22][OH:23].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[OH:23][CH2:22][CH2:21][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][CH2:11][C:12](=[O:19])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86708301HCID 86708301, compound

Product 1

HCID 86708302HCID 86708302, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of ethyl 2-[(2-hydroxyphenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.10 g, 0.38 mmol) which similarly prepared according to the procedure described in the Example 4, First step, 2-chloroethanol (0.038 mL, 0.57 mmol) and potassium carbonate (0.11 g, 0.80 mmol) in N,N-dimethylformamide (2.0 mL) was stirred at 90° C. for 2 days. Cooled to ambient temperature, ethyl acetate was added to the reaction mixture, the organic layer was washed with aqueous 5% citric acid solution, water and brine, dried over magnesium sulfate and concentrated. To the residue, tert-butyl methyl ether was added to precipitate the product. The precipitate was collected by filtration, washed with hexane then dried to afford ethyl 2-{[2-(2-hydroxyethoxy)phenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate as solid (0.041 g, y. 35%).

Workup

  1. temperatureCooled to ambient temperature
  2. washthe organic layer was washed with aqueous 5% citric acid solution, water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. additionTo the residue, tert-butyl methyl ether was added
  6. customto precipitate the product
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with hexane
  9. customthen dried

Sources & evidence

ORD record
ord-edd5b1437b2b49c3b3ac6f19743c547c
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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