Dichloromethane → 3-(5-Oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-benzaldehyde

HRID 2267044Notes

Reaction equation

HRID 2267044 reaction equation
[Cr]([O-])(OCl)(=O)=O.[NH+]1C=CC=CC=1.[OH:13][CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[NH:25][C:24](=[O:26])[O:23][N:22]=2)[CH:18]=[CH:19][CH:20]=1.ClCCl>O1CCCC1>[O:26]=[C:24]1[O:23][N:22]=[C:21]([C:17]2[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=2)[CH:14]=[O:13])[NH:25]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 1360829183-(3-hydroxymethyl-phenyl)-4H-[1,2,4]oxadiazol-5-oneHCID 178526120HCID 178526120, compound

Product 1

HCID 1360829193-(5-Oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-benzaldehydeYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add pyrdinium chloro chromate (5.22 g, 24.2 mmol) to a solution of 3-(3-hydroxymethyl-phenyl)-4H-[1,2,4]oxadiazol-5-one (3.10 g, 16.1 mmol) in tetrahydrofuran:dichloromethane (125 mL:125 mL) and stir. After 4 hours concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography eluting with ethyl acetate:hexanes:acetic acid (50%:50%:0.1%) to yield the title product as a white solid (2.20 g, 72%): 1H NMR (DMSO-d6) δ 7.83 (t, 1H), 8.10-8.17 (m, 2H), 8.35 (m, 1H), 10.09 (s, 1H), 13.15 (bs, 1H).

Workup

  1. concentrationAfter 4 hours concentrate under reduced pressure
  2. customto give a residue
  3. customPurify the residue by flash chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-8e84d090f24a480e9cd5e554a228a7a1
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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