Water → HCID 12762576, compound

HRID 724779Notes

Reaction equation

HRID 724779 reaction equation
O.C(=O)([O-])[O-].[K+].[K+].[CH2:8]([O:15][CH:16]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17]([O:19]CC1C=CC=CC=1)=[O:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[CH2:8]([O:15][CH:16]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17]([OH:19])=[O:18])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 11430Potassium CarbonateHCID 19710978HCID 19710978, compound

Product 1

HCID 12762576HCID 12762576, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Water (20 ml) and potassium carbonate (10.64 g) were added to a solution of benzyl dibenzyloxyacetate (11.15 g) in THF (80 ml) and the mixture heated under reflux for 24 hours. The mixture was allowed to cool, poured into water, extracted with ether, acidified with concentrated hydrochloric acid and again extracted with ether. The extract from acidic solution was washed with brine, dried (MgSO4) and evaporated under reduced pressure to give the sub-title compound (8.12 g), which was used crude in step c).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 24 hours
  3. temperatureto cool
  4. extractionextracted with ether
  5. extractionagain extracted with ether
  6. extractionThe extract from acidic solution
  7. washwas washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f8d74339b65946bf96da7efac409b945
Source dataset
uspto-grants-1998_01
Patent number
US05705456

Reaction notes

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