Ammonium cerium (IV) nitrate → 4-(3-Hydroxymethyl-[1,2,4]oxadiazol-5-ylmethyl)-benzoic acid ethyl ester

HRID 1717824Notes

Reaction equation

HRID 1717824 reaction equation
[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[CH2:23]([O:25][C:26](=[O:49])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]2[O:38][N:37]=[C:36]([CH2:39][O:40]C3C=CC(OC)=CC=3)[N:35]=2)=[CH:29][CH:28]=1)[CH3:24]>C(#N)C.O>[CH2:23]([O:25][C:26](=[O:49])[C:27]1[CH:28]=[CH:29][C:30]([CH2:33][C:34]2[O:38][N:37]=[C:36]([CH2:39][OH:40])[N:35]=2)=[CH:31][CH:32]=1)[CH3:24]

Participants

5

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrate2×HCID 666995654-[3-(4-Methoxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid ethyl ester

Product 1

HCID 666995924-(3-Hydroxymethyl-[1,2,4]oxadiazol-5-ylmethyl)-benzoic acid ethyl esterYield 528%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Add half of the ammonium cerium(IV) nitrate (285 mg, 0.52 mmol) to a solution of 4-[3-(4-methoxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid ethyl ester (193 mg, 0.52 mmol) in acetonitrile (9 mL) and water (2.3 mL) at room temperature. Stir the reaction mixture at room temperature for one hour and add the second half of the ammonium cerium(IV) nitrate (285 mg, 0.52 mmol). Stir at room temperature for an additional hour, dilute the reaction is with saturated aqueous sodium hydride CO3, stir for 5 minutes, dilute with water, and extract with ethyl acetate (3×). Wash the combined organic layers with brine, dry over MgSO4, and concentrate. Purify the residue by flash column chromatography using 50% ethyl acetate/hexane to give the title compound (720 mg, 81%). LC-MS (m/e): 263 (M+1).

Workup

  1. stirringStir at room temperature for an additional hour
  2. additiondilute the reaction
  3. stirringstir for 5 minutes
  4. extractionextract with ethyl acetate (3×)
  5. washWash the combined organic layers with brine
  6. dry with materialdry over MgSO4
  7. concentrationconcentrate
  8. customPurify the residue by flash column chromatography

Sources & evidence

ORD record
ord-05e20883b3d74322a7d37d917998e294
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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