Potassium Hydroxide → HCID 59583702, compound

HRID 1527718Notes

Reaction equation

HRID 1527718 reaction equation
[Cl:1][C:2]1[C:3]([CH:16]2[O:24][C:17]2([CH3:23])[C:18]([O:20]CC)=[O:19])=[C:4]([O:14][CH3:15])[C:5]2[C:10]([C:11]=1[O:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[OH-].[K+]>CCO>[Cl:1][C:2]1[C:3]([CH:16]2[O:24][C:17]2([CH3:23])[C:18]([OH:20])=[O:19])=[C:4]([O:14][CH3:15])[C:5]2[C:10]([C:11]=1[O:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59583681HCID 59583681, compound

Product 1

HCID 59583702HCID 59583702, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Darzens esters 70 (0.193 g, 0.550 mmol) were dissolved in EtOH (10.0 mL) and then KOH (0.200 g, 3.56 mmol) was added to the reaction. The reaction was heated to boiling and stirred at this temperature for 30 minutes. The reaction was then cooled, acidified, and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, and condensed. The resulting acid was then used as crude, or can be purified via flash chromatography (1:3 EtOAc:hexanes 0.5% AcOH) or recrystallization from Et2O/hexanes to provide 102 (0.179 g, 0.555 mmol, 101%) as a yellow oil made up of 4 diastereomers.

Workup

  1. temperatureThe reaction was heated
  2. temperatureThe reaction was then cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customcondensed
  8. customcan be purified via flash chromatography (1:3 EtOAc:hexanes 0.5% AcOH) or recrystallization from Et2O/hexanes

Sources & evidence

ORD record
ord-5b8fb4bb83c349409bdd0bef5ed09590
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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