Hydrogen Peroxide → (2S)-2-(4-fluorophenyl)pent-4-enoic acid

HRID 429476Notes

Reaction equation

HRID 429476 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:26])[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH2:16][CH:17]=[CH2:18])C1C=CC=CC=1.[O:27]1CCCC1.O.[OH-].[Li+].OO>[OH-].[Na+].O>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C@H:15]([CH2:16][CH:17]=[CH2:18])[C:14]([OH:26])=[O:27])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 15536020(S)-4-benzyl-3-(2-(4-fluorophenyl)pent-4-enoyl)-2-oxazolidinone

Product 1

HCID 15536021(2S)-2-(4-fluorophenyl)pent-4-enoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Combine (S)-4-benzyl-3-(2-(4-fluorophenyl)pent-4-enoyl)-2-oxazolidinone (9.66 g, 27.34 mol), tetrahydrofuran (160 mL), and water (40 mL). Cool in an ice bath. Add lithium hydroxide hydrate (2.52 g, 60 mmol) and an aqueous solution of hydrogen peroxide (10 mL, 30% 116 mmol). After 3 hours, dilute the 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 concentrated hydrochloric acid solution (about 15 mL), 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-(4-fluorophenyl)pent-4-enoic acid.

Workup

  1. temperatureCool in an ice bath
  2. extractionextract twice with diethyl ether
  3. temperatureCool the aqueous layer in an ice bath
  4. extractionextract twice with dichloromethane
  5. extractionExtract the combined organic layers with a saturated aqueous sodium thiosulfate solution
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-624d8ae2d531480fa15c2353251c83fe
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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