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Acetic Anhydride → HCID 59792534, compound

HRID 1645562
Notes
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Reaction equation

HRID 1645562 reaction equation
[CH2:1]1[C:4]2([O:9][CH2:8][CH:7]([CH2:10][O:11][C:12]3[C:17]([CH3:18])=[CH:16][N+:15]([O-])=[C:14]([CH3:20])[C:13]=3[CH3:21])[CH2:6][O:5]2)[CH2:3][CH2:2]1.C(OC(=O)C)(=[O:24])C.[OH-].[Na+]>CO>[CH2:1]1[C:4]2([O:9][CH2:8][CH:7]([CH2:10][O:11][C:12]3[C:17]([CH3:18])=[CH:16][N:15]=[C:14]([CH2:20][OH:24])[C:13]=3[CH3:21])[CH2:6][O:5]2)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 59792344Pyridine, 4-(5,9-dioxaspiro[3.5]non-7-ylmethoxy)-2,3,5-trimethyl-, 1-oxide

Product 1

HCID 59792534HCID 59792534, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

The 4-(5,9-dioxaspiro[3.5]non-7-ylmethoxy)-2,3,5-trimethylpyridine 1-oxide (1.97 g, 6.72 mmol) obtained in the step (13b) was mixed with acetic anhydride (20 ml, 212 mmol). The mixture was stirred at 85° C. for 1.5 hours. After cooled to room temperature, the reaction mixture was concentrated. To the residue, methanol (20 ml) and a 5N aqueous sodium hydroxide solution (20 ml, 100 mmol) were added and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was concentrated and the residue was partitioned between water and ethyl acetate. The organic layer was washed with a 2N aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain the title compound (1.69 g, yield: 85.7%) as a brown oil.

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. stirringthe mixture was stirred at room temperature for 45 minutes
  4. concentrationThe reaction mixture was concentrated
  5. customthe residue was partitioned between water and ethyl acetate
  6. washThe organic layer was washed with a 2N aqueous sodium hydroxide solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-28363176e5e14583858fde116548cad3
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08124780B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes