Pyridine → HCID 15462825, compound

HRID 1357194Notes

Reaction equation

HRID 1357194 reaction equation
N1C=CC=CC=1.[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25]1[O:30][C:29](=[O:31])[C:28]([CH3:32])=[C:27]([OH:33])[C:26]=1[CH3:34].OS([O-])(=O)=O.[K+]>C(Cl)Cl>[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25]1[O:30][C:29](=[O:31])[C:28]([CH3:32])=[C:27]([O:33][C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:26]=1[CH3:34]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 516920Potassium bisulfateHCID 54712960HCID 54712960, compound

Product 1

HCID 15462825HCID 15462825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (64 μl) and benzoyl chloride (45 μl) were added to a suspension of 6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one (40 mg) in CH2Cl2 (5 ml), and the mixture was stirred at room temperature for 50 minutes. The reaction solution was poured into a KHSO4 aqueous solution and extracted with AcOEt, and the organic layer was rinsed with saturated saline and dried with MgSO4, and then filtered and concentrated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=5/1→4/1) to obtain 6-(benzofuran-2-yl)-4-benzoyloxy-3,5-dimethyl-2H-pyran-2-one.

Workup

  1. extractionextracted with AcOEt
  2. washthe organic layer was rinsed with saturated saline
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=5/1→4/1)

Sources & evidence

ORD record
ord-d59aadcce2b848bdad78acede6fa6d89
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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