4H-pyran-4-one → HCID 22419713, compound

HRID 1720038Notes

Reaction equation

HRID 1720038 reaction equation
O1[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[C:8]([O:12][C:13](=[O:16])[NH:14][NH2:15])([CH3:11])([CH3:10])[CH3:9]>C(O)C>[C:8]([O:12][C:13]([NH:14][N:15]1[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1)=[O:16])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 79684H-pyran-4-oneHCID 70091tert-Butyl carbazate

Product 1

HCID 22419713HCID 22419713, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Pyranone (1 g, 10.4 mmol) and t-butylcarbazate (1.32 g, 10 mmol) were heated at reflux in ethanol for 48 h. The solvent was gradually allowed to distil from the mixture and the residue was chromatographed on silica gel 60, eluting with ethanol, dichloromethane (1:19) to give the title compound (1.16 g, 50%); υmax (KBr) 1723, 1630, and 1550cm-1 ; δH 1.54 (9H, s), 6.47 (2H, d), and 7.60 (2H, d); M+ 210.

Workup

  1. customto distil from the mixture
  2. customthe residue was chromatographed on silica gel 60
  3. washeluting with ethanol, dichloromethane (1:19)

Sources & evidence

ORD record
ord-42ef426f133947988f61217964b3607c
Source dataset
uspto-grants-1996_04
Patent number
US05504076

Reaction notes

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