Methane → HCID 54496068, compound

HRID 1029707Notes

Reaction equation

HRID 1029707 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])O)[C:5]([OH:6])=[C:3]1[OH:4].[CH3:13][S:14][CH2:15][C:16]1(OC)[CH:20]=[CH:19][CH:18](OC)[O:17]1.[O:25]1C=CCC1.C>O.C(OCC)(=O)C>[CH3:13][S:14][CH2:15][C:16]1[O:17][C:18]([C:3]2([OH:4])[C:5](=[O:6])[CH:7]([CH2:9][CH:11]([OH:12])[OH:25])[O:8][C:2]2=[O:1])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 709342,3-DihydrofuranHCID 19900858HCID 19900858, compoundHCID 54670067L-Ascorbic Acid

Product 1

HCID 54496068HCID 54496068, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

L-Ascorbic acid (8.8 g, 0.05 mole) was dissolved in 62 mL water that had been purged with nitrogen for 1 hour. Freshly distilled 2-methylthiomethyl-2,5-dimethoxy-2,5-dihydrofuran (9.5 g, 0.05 mole) was added dropwise with stirring over a period of 1 hour. The reaction mixture was not completely homogeneous. Twenty four hours after the addition of the dihydrofuran, the insoluble droplets were removed by treatment with methylene chloride. The aqueous fraction was frozen and freeze-dried to give 14.2 g (98%) crude product. The amorphous solid was dissolved in 100 mL ethyl acetate and was shaken with 3 g decolorizing charcoal and 3 g celite. After filtration, the solvent was removed under vacuum to give 12.7 g (88%) amorphous product, sinters 40°-42° C.

Workup

  1. customhad been purged with nitrogen for 1 hour
  2. customthe insoluble droplets were removed by treatment with methylene chloride
  3. temperatureThe aqueous fraction was frozen
  4. customfreeze-dried
  5. customto give 14.2 g (98%) crude product
  6. stirringwas shaken with 3 g
  7. filtrationAfter filtration
  8. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2f33cb5611f444a685cb5f917f938d9e
Source dataset
uspto-grants-1992_04
Patent number
US05102909

Reaction notes

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