Acetic Acid → HCID 69431813, compound

HRID 1295335Notes

Reaction equation

HRID 1295335 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:38])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH:23]([C:30](=O)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=O)=[CH:15][CH:14]=2)[N:10]=1.C([O-])(=O)C.[NH4+:43].C(O)(=O)C>C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:38])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]3[O:22][C:23]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[C:30]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:43]=3)=[CH:15][CH:14]=2)[N:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 69428124HCID 69428124, compound

Product 1

HCID 69431813HCID 69431813, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]phenyl]acetoxy-5-oxo-5-phenylpentanoate (1.49 g), ammonium acetate (777 mg) and acetic acid (5 ml) was refluxed for 3 hrs. After cooling, ethyl acetate was added to the reaction mixture. The obtained ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate and then saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-[2-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-4-phenyl-5-oxazolyl]propionate (1.11 g, yield 77%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio).

Workup

  1. temperaturewas refluxed for 3 hrs
  2. temperatureAfter cooling
  3. washThe obtained ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialsaturated brine, dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-177e7061a6084af385e2c15cacc919ce
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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