Water → HCID 12762576, compound

HRID 2294629Notes

Reaction equation

HRID 2294629 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>O1CCCC1>[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, prepared as described in Step 1 above) in tetrahydrofuran (80 ml) and the mixture heated under reflux for twenty-four hours. It 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 over magnesium sulphate and evaporated under reduced pressure to give the title compound (8.12 g), used crude in Step 3.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for twenty-four 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 over magnesium sulphate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-516b8fb2f6594c8e85a412bb174eb5c7
Source dataset
uspto-grants-1997_11
Patent number
US05688962

Reaction notes

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