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

HRID 1818550Notes

Reaction equation

HRID 1818550 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[OH:12][CH2:13][C:14]1[CH:15]=[C:16]([C:20]2[NH:24][C:23](=[O:25])[O:22][N:21]=2)[CH:17]=[CH:18][CH:19]=1.ClCCl>O1CCCC1>[O:25]=[C:23]1[O:22][N:21]=[C:20]([C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[CH:13]=[O:12])[NH:24]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 1360829183-(3-hydroxymethyl-phenyl)-4H-[1,2,4]oxadiazol-5-oneHCID 178418287HCID 178418287, 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 PCC (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-6ed21c675e29473ca1af09333feb4e84
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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