Acetic Anhydride → HCID 86592830, compound

HRID 1592947Notes

Reaction equation

HRID 1592947 reaction equation
[C:1]([Mg]Cl)#[CH:2].[CH2:5]([O:7][CH2:8][C:9]([CH2:11][O:12][CH2:13][CH3:14])=[O:10])[CH3:6].[C:15](OC(=O)C)(=[O:17])[CH3:16].[Cl-].[NH4+]>C1COCC1>[CH2:5]([O:7][CH2:8][C:9]([O:10][C:15](=[O:17])[CH3:16])([CH2:11][O:12][CH2:13][CH3:14])[C:1]#[CH:2])[CH3:6]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 2273461,3-diethoxyacetoneHCID 178462451HCID 178462451, compound

Product 1

HCID 86592830HCID 86592830, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (360 mL, 180 mmol) of ethynyl magnesium chloride in 0.5 M THF was stirred under ice-cooling and 1,3-diethoxyacetone (21.93 g, 150 mmol) was added dropwise. The mixture was stirred under ice-cooling for 30 min and acetic anhydride (18.4 mL, 195 mmol) was added dropwise. The mixture was stirred at room temperature for 1 hr. After the completion of the reaction, aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give acetic acid 1,1-bis-ethoxymethyl-2-propynyl ester (31.36 g, 97%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 min
  3. stirringThe mixture was stirred at room temperature for 1 hr
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-21b0ac09a2d34e7eb9ca8e122e9c48fe
Source dataset
uspto-grants-2007_11
Patent number
US07294629B2

Reaction notes

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