Acetic Acid → HCID 54327247, compound

HRID 726442Notes

Reaction equation

HRID 726442 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1.C(O)(=[O:20])C>O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:20])[C:9]1[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 18997525HCID 18997525, compound

Product 1

HCID 54327247HCID 54327247, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (620 mg) obtained in the above (1) is dissolved in a mixture of acetic acid (30 ml) and water (5 ml), and thereto is added chromic anhydride (1.3 g)/acetic acid (2 ml), and the mixture is stirred at room temperature for 17.5 hours. The mixture is diluted with ethyl acetate, and washed with a saturated aqueous sodium hydrogen carbonate solution, and purified by silica gel column chromatography (n-hexane/ethyl acetate=5:1→2:1) to give the title compound (70 mg, 11%), and the starting compound (365 mg, 59%) is also recovered.

Workup

  1. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  2. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=5:1→2:1)

Sources & evidence

ORD record
ord-6acf26b3769d4592bc2b6c14c786a48b
Source dataset
uspto-grants-1998_01
Patent number
US05707994

Reaction notes

Loading…