Acetic Anhydride → HCID 67246495, compound

HRID 2425011Notes

Reaction equation

HRID 2425011 reaction equation
Cl(O)(=O)(=O)=O.[CH3:6][C:7](OC(C)=O)=[O:8].[CH2:13]([O:15][C:16](=[O:32])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:14]>C(Cl)Cl>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][O:25][C:20]1[CH:21]=[CH:22][C:23]([C:7](=[O:8])[CH3:6])=[CH:24][C:19]=1[O:18][CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24247Perchloric AcidHCID 12678066HCID 12678066, compound

Product 1

HCID 67246495HCID 67246495, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Perchloric acid (70% aq.; 1.0 ml) was added slowly to freshly distilled Ac2O (25 ml) at 0° C. The compound of example 20a (31.8 g; 125 mmol) in CH2Cl2 (13 ml) was added drop wise at 10-15° C. The reaction mixture was heated on steam bath for 1 h, concentrated, poured over crushed ice and NaHCO3 (˜25 g) and extracted with ether. The ether layer was washed with brine, dried (Na2SO4), concentrated and purified using flash chromatography (silica gel, 5% CH3CN in CHCl3) to obtain the title compound. Yield, 24.6 g (61.5%), semisolid; analysis: C16H20O7: requires C, 59.25; H, 6.22. found: C, 59.57; H, 6.28%.

Workup

  1. temperatureThe reaction mixture was heated on steam bath for 1 h
  2. concentrationconcentrated
  3. additionpoured
  4. customover crushed ice and NaHCO3 (˜25 g)
  5. extractionextracted with ether
  6. washThe ether layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. custompurified

Sources & evidence

ORD record
ord-535506ce65024d7c96101a7eab0d41ea
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

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