Hydrogen Peroxide → (S)-2-phenylpent-4-enoic acid

HRID 1584494Notes

Reaction equation

HRID 1584494 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:25])[CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][CH:17]=[CH2:18])C1C=CC=CC=1.[O:26]1CCCC1.O.[OH-].[Li+].OO>O>[C:19]1([C@H:15]([CH2:16][CH:17]=[CH2:18])[C:14]([OH:25])=[O:26])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 54574304HCID 54574304, compound

Product 1

HCID 12086387(S)-2-phenylpent-4-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine (S)-4-benzyl-3-(2-phenylpent-4-enoyl)-2-oxazolidinone (3.35 g, 10 mol), tetrahydrofuran (80 mL), and water (20 mL). Cool in an ice bath. Add lithium hydroxide hydrate (0.84 g, 20 mmol) and an aqueous solution of hydrogen peroxide (4 mL, 30%, 46.4 mmol). After 3 hours, concentrate the reaction mixture to about half volume, dilute the concentrated reaction mixture with an aqueous 1 M sodium hydroxide solution and extract twice with diethyl ether. Cool the aqueous layer in an ice bath, acidify with an aqueous 3 M hydrochloric acid solution, and extract twice with dichloromethane. Extract the combined organic layers with a saturated aqueous sodium thiosulfate solution, dry over MgSO4, filter, and evaporate in vacuo to give (S)-2-phenylpent-4-enoic acid: Rf =0.48 (silica gel, 5% methanol/dichloromethane).

Workup

  1. temperatureCool in an ice bath
  2. concentrationconcentrate the reaction mixture to about half volume
  3. additiondilute
  4. customthe concentrated reaction mixture with an aqueous 1 M sodium hydroxide solution
  5. extractionextract twice with diethyl ether
  6. temperatureCool the aqueous layer in an ice bath
  7. extractionextract twice with dichloromethane
  8. extractionExtract the combined organic layers with a saturated aqueous sodium thiosulfate solution
  9. dry with materialdry over MgSO4
  10. filtrationfilter
  11. customevaporate in vacuo

Sources & evidence

ORD record
ord-d33bdd7d1dbb4952b6b24b35edbfa2c0
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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