Isopropanol → HCID 54550111, compound

HRID 1492567Notes

Reaction equation

HRID 1492567 reaction equation
[OH:1][CH:2]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:3][C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[O:1]=[C:2]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:3][C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 53632560HCID 53632560, compoundHCID 131709961Jones' reagent

Product 1

HCID 54550111HCID 54550111, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 4-[2-hydroxy-2-(3-pyridyl)ethyl]-α-methylcinnamate (1.84 g) was dissolved in 60 ml of acetone, followed by dropwise addition of 2.27 g of 2.67M Jones Reagent, and stirred for 30 minutes. After addition of 2 ml of isopropanol, the resulting mixture was concentrated under reduced pressure, followed by addition of water for extraction with ethyl acetate. The organic phase was washed in saturated aqueous sodium and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column, and from a fraction eluted with chloroform-methanol(98:2 v/v) was obtained 0.77 g of ethyl 4-[2-oxo-2-(3-pyridyl)ethyl]-α-methylcinnamate.

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. additionfollowed by addition of water for extraction with ethyl acetate
  3. washThe organic phase was washed in saturated aqueous sodium
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue obtained
  7. washfrom a fraction eluted with chloroform-methanol(98:2 v/v)

Sources & evidence

ORD record
ord-597e7cfa42e44071b275e05bd878db73
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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