Methanol → HCID 15232720, compound

HRID 257617Notes

Reaction equation

HRID 257617 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29]O>S(=O)(=O)(O)O.C(OCC)C>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 1319604,5-Diphenyl-2-oxazolenonanoic acid

Product 1

HCID 15232720HCID 15232720, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4,5-diphenyl-2-oxazole nonanoic acid (800 mg, 2 mmol), methanol (2 mL) and concentrated sulfuric acid (2 drops) was heated to reflux. After 2 hours, the solvent was evaporated and the residue partitioned between CH2Cl2 and water. The organic phase was separated, washed with saturated NaHCO3 solution, dried over sodium sulfate and concentrated in vacuo to leave an oil. Chromatography on a column of silica gel using a mixture of hexanes and diethyl ether (4:1) as eluent gave methyl 4,5-diphenyl-2-oxazolenonanoate (800 mg, 96%).

Workup

  1. temperaturewas heated to reflux
  2. customthe solvent was evaporated
  3. customthe residue partitioned between CH2Cl2 and water
  4. customThe organic phase was separated
  5. washwashed with saturated NaHCO3 solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto leave an oil

Sources & evidence

ORD record
ord-78f90e43addb4234ade53f9ce9039d2e
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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