Ethyl orthoformate → HCID 131721574, compound

HRID 849383Notes

Reaction equation

HRID 849383 reaction equation
[C:1]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:10])[C@H:2]([C@@H:4]([C:6]([O:8][CH3:9])=[O:7])[OH:5])[OH:3].[CH:25](OCC)(OCC)[O:26][CH2:27][CH3:28]>C1(C)C=CC=CC=1>[CH2:27]([O:26][CH:25]1[O:5][C@H:4]([C:6]([O:8][CH3:9])=[O:7])[C@@H:2]([C:1]([O:11][CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:10])[O:3]1)[CH3:28]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 10520437HCID 10520437, compound

Product 1

HCID 131721574HCID 131721574, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

400 mg of diphenylmethyl methyl D-tartarate was dissolved in 7 ml of toluene, and a catalytic amount of Amberlyst 15 and 1 ml of triethyl orthoformate were added, followed by refluxing under heating for one hour. Amberlyst was filtered off. Then, the filtrate was extracted by an addition of water and ethyl acetate. The organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 195 mg of the above identified compound as a colorless oily substance.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for one hour
  3. filtrationAmberlyst was filtered off
  4. extractionThen, the filtrate was extracted by an addition of water and ethyl acetate
  5. washThe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution
  6. dry with materiala saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate
  7. filtrationThe drying agent was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)
  10. customto obtain 195 mg of the

Sources & evidence

ORD record
ord-011033b0db344bb3932da6ff00b304a7
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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