Ethyl Acetate → 4-(3-Hydroxymethyl-[1,2,4]oxadiazol-5-ylmethyl)-benzoic acid ethyl ester

HRID 1818592Notes

Reaction equation

HRID 1818592 reaction equation
[N+:1]([O-:4])([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]2ON=[C:36]([CH2:39][O:40]C3C=CC(OC)=CC=3)[N:35]=2)=[CH:29][CH:28]=1)[CH3:24].[Na].C(OCC)(=O)C>C(#N)C.O>[CH2:23]([O:25][C:26](=[O:49])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]2[O:4][N:1]=[C:36]([CH2:39][OH:40])[N:35]=2)=[CH:29][CH:28]=1)[CH3:24]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 5360545SodiumHCID 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 hydrideCO3, stir for 5 minutes, dilute with water, and extracte 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. washWash the combined organic layers with brine
  5. dry with materialdry over MgSO4
  6. concentrationconcentrate
  7. customPurify the residue by flash column chromatography

Sources & evidence

ORD record
ord-7562cfaf51ed426788bbf79f19686720
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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