Acetic Anhydride → HCID 59792362, compound

HRID 1645540Notes

Reaction equation

HRID 1645540 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][CH2:11][C:12]2([CH2:18][CH2:19][CH3:20])[O:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:5]=[CH:4][N+:3]=1[O-].C(OC(=O)C)(=[O:24])C>>[CH3:8][C:7]1[C:2]([CH2:1][OH:24])=[N:3][CH:4]=[CH:5][C:6]=1[O:9][CH2:10][CH2:11][C:12]1([CH2:18][CH2:19][CH3:20])[O:17][CH2:16][CH2:15][CH2:14][O:13]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 59792601HCID 59792601, compound

Product 1

HCID 59792362HCID 59792362, compoundYield 43.3%

Conditions

Temperature
90 °C

Procedure

The 2,3-dimethyl-4-(2-(2-propyl-1,3-dioxan-2-yl)ethoxy)pyridine 1-oxide (3.9 g, 13.2 mmol) obtained in the step (8c) was mixed with acetic anhydride (16 ml). The mixture was stirred at 90° C. for 2 hours. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue, methanol (20 ml) and a 5N aqueous sodium hydroxide solution (10 ml) were added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated and the residue was separated by use of a saturated saline solution and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated, and the residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate, ethyl acetate/methanol) to obtain the title compound (1.69 g, yield: 43.3%) as a yellow oil.

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue, methanol (20 ml) and a 5N aqueous sodium hydroxide solution (10 ml) were added
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was separated by use of a saturated saline solution and ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-ce95f3ddc3f24fac9ed568d60fd8cf0c
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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