Water → HCID 11652706, compound

HRID 2244469Notes

Reaction equation

HRID 2244469 reaction equation
[OH-].[K+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[CH:28]=[CH:27][C:11]([O:12][C@@H:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:14]([O:16]CC)=[O:15])=[CH:10][CH:9]=1.O>C(O)C>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[CH:9]=[CH:10][C:11]([O:12][C@@H:13]([CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:14]([OH:16])=[O:15])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67031112HCID 67031112, compound

Product 1

HCID 11652706HCID 11652706, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

21.5 mmol of potassium hydroxide are added to a solution of 4.3 mmol of ethyl (2S)-2-(4-furan-2-ylphenoxy)-4-phenylbutanoate, obtained in the preceding example, in 30 ml of ethanol. The mixture is refluxed for 30 minutes, 15 ml of water are added and refluxing is continued for 3 hours 30 minutes. After cooling to room temperature, the ethanol is evaporated off under vacuum. The product is taken up in water and washed with ether. The aqueous phase is acidified with 10% hydrochloric acid. A white precipitate forms, which is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and evaporated under vacuum. 1.2 g of a beige-coloured solid, that recrystallizes from a hexane/ethyl acetate mixture to give 1 g of a solid melting at 140-142° C., are obtained.

Workup

  1. temperatureThe mixture is refluxed for 30 minutes
  2. temperaturerefluxing
  3. customthe ethanol is evaporated off under vacuum
  4. washwashed with ether
  5. extractionA white precipitate forms, which is extracted with ethyl acetate
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customevaporated under vacuum
  8. custom1.2 g of a beige-coloured solid, that recrystallizes from a hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-37238718b73643a9b1f0d83c542a75e6
Source dataset
uspto-grants-2010_03
Patent number
US07678831B2

Reaction notes

Loading…