Hydrogen Peroxide → (S)-2-(3,4-dichlorophenyl)pent-4-enoic acid

HRID 429469Notes

Reaction equation

HRID 429469 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:27])[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[CH2:16][CH:17]=[CH2:18])C1C=CC=CC=1.[O:28]1CCCC1.O.[OH-].[Li+].OO>O>[Cl:26][C:21]1[CH:20]=[C:19]([C@H:15]([CH2:16][CH:17]=[CH2:18])[C:14]([OH:27])=[O:28])[CH:24]=[CH:23][C:22]=1[Cl:25]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 53834151(S)-4-benzyl-3-(2-(3,4-dichlorophenyl)pent-4-enoyl)-2-oxazolidinone

Product 1

HCID 15261879(S)-2-(3,4-dichlorophenyl)pent-4-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine (S)-4-benzyl-3-(2-(3,4-dichlorophenyl)pent-4-enoyl)-2-oxazolidinone (13.7 g, 34.0 mol), tetrahydrofuran (300 mL), and water (60 mL). Cool in an ice bath. Add lithium hydroxide hydrate (1.7 g, 71.0 mmol) and an aqueous solution of hydrogen peroxide (12 mL, 30% 140 mmol). After 2 hours, quench by the addition of an aqueous 10% sodium thiosulfate solution (100 mL). Add 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 concentrated hydrochloric acid solution (about 20 mL), and extract twice with dichloromethane. Combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give (S)-2-(3,4-dichlorophenyl)pent-4-enoic acid.

Workup

  1. temperatureCool in an ice bath
  2. customquench by the addition of an aqueous 10% sodium thiosulfate solution (100 mL)
  3. additionAdd an aqueous 1 M sodium hydroxide solution
  4. extractionextract twice with diethyl ether
  5. temperatureCool the aqueous layer in an ice bath
  6. extractionextract twice with dichloromethane
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo

Sources & evidence

ORD record
ord-089bb92d07d34c64b82b65aab6850821
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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