Sodium Bicarbonate → HCID 18367786, compound

HRID 379885Notes

Reaction equation

HRID 379885 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:10]=[CH:9][O:8][C:7]=1[C:11](=[O:13])[CH3:12])(=[O:3])[CH3:2].[Br-:14].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH:10]=[CH:9][O:8][C:7]=1[C:11](=[O:13])[CH2:12][Br:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18368211HCID 18368211, compoundHCID 21124087Pyridiniumtribromide

Product 1

HCID 18367786HCID 18367786, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Acetoxymethyl-2-acetylfuran (1.7 g, 9.3 mmol, prepared according to the procedure described in Acta. Chemica. Scandinavia, 1990, 44, 916) was dissolved in acetic acid (30 ml). To the solution was added pyridinium tribromide (3.3 g, 10.2 mmol) and the resulting mixture was stirred at room temperature for 3 h. The mixture was cooled to 0° C. and saturated aqueous sodium bicarbonate added dropwise until the solution was basic. The mixture was extracted with ethyl acetate (100 ml). The organic extract was washed with brine (100 ml), dried (MgSO4) and concentrated to give 2.3 g (95%) of the title compound. 1H-NMR (CDCl3) δ: 7.54 (1 H, d, J=1.6 Hz), 6.65 (1 H, d, J=1.6 Hz), 5.38 (2 H, s), 4.37 (2 H, s), 2.09 (3 H, s).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionThe mixture was extracted with ethyl acetate (100 ml)
  3. extractionThe organic extract
  4. washwas washed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e78934829f3477693353d965bd8ccb7
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

Loading…