Ethylene Glycol → HCID 18779157, compound

HRID 1422363Notes

Reaction equation

HRID 1422363 reaction equation
C(N[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:9]=1CCCC)=[O:7])(C)(C)C.[ClH:24].[CH2:25]([OH:28])[CH2:26]O>>[CH2:6]([C:12]1[CH:13]=[C:8]([CH:9]=[CH:10][C:11]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:6]([O:28][CH2:25][CH2:26][Cl:24])=[O:7])[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 54305770HCID 54305770, compound

Product 1

HCID 18779157HCID 18779157, compound

Procedure

To a 200 mL round bottomed flask with a stirring bar and a reflux condenser was added (N-tert-butyl)-3-butyl-4-biphenylcarboxamide (3.17 g, 10.24 mmol), ethylene glycol (25 mL) and 12N HCl (25 mL). This mixture was heated at reflux 72 h. The cooled mixture was extracted with EtOAc and the EtOAc extracts were combined, washed with H2O (3×) and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an oil. This material was chromatographed on silica gel using 30% EtOAc in hexane as eluantto afford the title compound as an oil.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux 72 h
  3. extractionThe cooled mixture was extracted with EtOAc
  4. washwashed with H2O (3×) and brine
  5. customDrying
  6. filtration(MgSO4), filtration and removal of the solvent in vacuo
  7. customgave an oil
  8. customThis material was chromatographed on silica gel using 30% EtOAc in hexane as eluantto

Sources & evidence

ORD record
ord-d8b624fdf7c64fe3a65cef9fe82afcaf
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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