Allyl iodide → (S)-4-benzyl-3-(2-(4-fluorophenyl)pent-4-enoyl)-2-oxazolidinone

HRID 1584485Notes

Reaction equation

HRID 1584485 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[CH2:34](I)[CH:35]=[CH2:36].[Cl-].[NH4+]>C(OCC)(=O)C.CCCCCC.O1CCCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[CH:15]([C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[CH2:36][CH:35]=[CH2:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11166Allyl iodideHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 15536019(S)-4-Benzyl-3-(2-(4-fluorophenyl)acetyl)oxazolidin-2-one

Product 1

HCID 15536020(S)-4-benzyl-3-(2-(4-fluorophenyl)pent-4-enoyl)-2-oxazolidinone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine (S)-4-benzyl-3-(4-fluorophenyl)acetyl-2-oxazolidinone (14.28 g, 45.6 mmol) and tetrahydrofuran (150 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of sodium hexamethyldisilazide (50 mL, 1.0 M in tetrahydrofuran, 50 mmol). After 25 minutes, add allyl iodide (13 mL, 142.2 mmol) and then replace the bath with a dry-ice/carbon tetrachloride bath. After 1 hour, quench the reaction by the addition of a saturated aqueous ammonium chloride solution, extract with diethyl ether, and separate the layers. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/6 ethyl acetate/hexane. Combine the product containing fractions, evaporate, and recrytallize from chloroform/hexane to give (S)-4-benzyl-3-(2-(4-fluorophenyl)pent-4-enoyl)-2-oxazolidinone: mp; 103-104° C. Rf =0.57 (silica gel, 20% ethyl acetate/hexane).

Workup

  1. temperatureCool in a dry-ice/acetone bath
  2. waitAfter 1 hour
  3. customquench
  4. customthe reaction
  5. extractionextract with diethyl ether
  6. customseparate the layers
  7. dry with materialDry the organic layer over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue
  11. additioncontaining fractions
  12. customevaporate

Sources & evidence

ORD record
ord-0f39acd018ca4b128eec4f9e766d0462
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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