Methane → HCID 57295602, compound

HRID 1734244Notes

Reaction equation

HRID 1734244 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=[O:3])C.[C:8]([O:11][CH2:12][C@H:13]1[C@H:17]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[O:16][CH2:15][O:14]1)(=[O:10])[CH3:9].C.[C:24](=O)([O-])O.[Na+]>[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C.C(O)(=O)C>[C:5]([O:4][CH2:1][O:3][C@H:13]([C@@H:17]([O:16][C:15](=[O:14])[CH3:24])[CH2:18][O:19][C:20](=[O:22])[CH3:21])[CH2:12][O:11][C:8](=[O:10])[CH3:9])(=[O:7])[CH3:6]

Participants

8

Reactant 4

HCID 297MethaneHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 14157594HCID 14157594, compound

Product 1

HCID 57295602HCID 57295602, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalyst2×HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

100.2 g of acetic anhydride was added to 61.0 g of (4S,5S)-4,5-bis(acetoxymethyl)-1,3-dioxolane obtained in Example 15. To this was added 11.8 g of glacial acetic acid to dissolve the mixture. 3.4 g of anhydrous zinc chloride was added while stirring. The zinc chloride was slowly dissolved to change the color of the mixture from yellow into charcoal. After the reaction overnight, the reaction mixture was charged into a separating funnel which contained 500 ml of ethyl acetate. To this was added saturated aqueous solution of sodium hydrogen carbonate to neutralize. After washing with water and drying, the product was concentrated by evaporator. Acetic anhydride not decomposed was removed by a chemical pump to obtain 91.9 g (yield: 87.7%) of an yellow oil of the title compound.

Workup

  1. dissolutionto dissolve the mixture
  2. customAfter the reaction overnight
  3. additionthe reaction mixture was charged into a separating funnel which
  4. washAfter washing with water
  5. customdrying
  6. concentrationthe product was concentrated by evaporator
  7. customAcetic anhydride not decomposed was removed by a chemical pump

Sources & evidence

ORD record
ord-340605c0fbbc41eab560fddaccb5a988
Source dataset
uspto-grants-1996_07
Patent number
US05532380

Reaction notes

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