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

HRID 1584486Notes

Reaction equation

HRID 1584486 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.C(OCC)C.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

8

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 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Alternately, combine (S)-4-benzyl-3-(4-fluorophenyl)acetyl-2-oxazolidinone (43.08 g, 426 mmol) and tetrahydrofuran (450 ml). Cool in a dry-ice acetone bath. Add dropwise a solution of sodium hexamethyldisilazide (153.0 ml, 1 M in tetrahydrofuran, 137.5 mmol). After 40 minutes, add a solution of allyl iodide (39.0 ml, 426 mmol) and replace the bath with a dry-ice/carbon tetrachloride bath. After 1.5 hours, quench the reaction by the addition of a saturated aqueous solution of ammonium chloride, add diethyl ether (200 ml), and stir. After about 30 minutes, separate the layers and extract the aqueous layer twice with diethyl ether. Dry the combined organic layers over MgSO4, filter, and evaporate in vacuo to give a residue. Dry the residue in a vacuum, dissolve in ethyl acetate (about 400 ml), and extract with a saturated aqueous sodium thiosulfate solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 13% ethyl acetate/hexane to give (S)-4-benzyl-3-(2-(4-fluorophenyl)pent-4-enoyl)-2-oxazolidinone.

Workup

  1. temperatureCool in a dry-ice acetone bath
  2. waitAfter 1.5 hours
  3. customquench
  4. customthe reaction
  5. waitAfter about 30 minutes
  6. customseparate the layers
  7. extractionextract the aqueous layer twice with diethyl ether
  8. dry with materialDry the combined organic layers over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue
  12. customDry the residue in a vacuum
  13. dissolutiondissolve in ethyl acetate (about 400 ml)
  14. extractionextract with a saturated aqueous sodium thiosulfate solution
  15. dry with materialDry the organic layer over MgSO4
  16. filtrationfilter
  17. customevaporate in vacuo
  18. customto give a residue

Sources & evidence

ORD record
ord-aad2f1b12c7b47068d9ab5eba1f61b13
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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