Sodium Chloride → HCID 54574304, compound

HRID 429482Notes

Reaction equation

HRID 429482 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:22])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:33](I)[CH:34]=[CH2:35].[Cl-].[Na+]>C(OCC)(=O)C.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:22])[CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:35][CH:34]=[CH2:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 11166Allyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 11130206(4S)-3-(2-Phenylacetyl)-4-(phenylmethyl)-2-oxazolidinone

Product 1

HCID 54574304HCID 54574304, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Alternately, combine (S)-4-benzyl-3-phenylacetyl-2-oxazolidinone (8.0 g, 27 mmol) and tetrahydrofuran (50 mL). cool in a dry-ice/acetone bath. Add dropwise a solution of sodium bis(trimethylsilyl)amide (30 mL, 1.0 M in tetrahydrofuran, 30 mmol). After 30 minutes, add allyl iodide (9.1 g, 54 mmol) and then replace the bath with a dry-ice/carbon tetrachloride bath. After 1.5 hours, quench the reaction by the addition of a saturated aqueous sodium chloride solution, extract with diethyl ether, and separate the layers. Extract the aqueous layer three times with diethyl ether. Combine the organic layers, extract with an aqueous 1 M hydrochloric acid solution, a saturated aqueous sodium bicarbonate solution, dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Dissolve in ethyl acetate, extract with a saturated aqueous sodium thiosulfate solution, dry the over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10% ethyl acetate/hexane. Combine the product containing fractions, evaporate, and recrytallize from chloroform/hexane to give (S)-4-benzyl-3-(2-phenylpent-4-enoyl)-2-oxazolidinone.

Workup

  1. temperaturecool in a dry-ice/acetone bath
  2. waitAfter 1.5 hours
  3. customquench
  4. customthe reaction
  5. extractionextract with diethyl ether
  6. customseparate the layers
  7. extractionExtract the aqueous layer three times with diethyl ether
  8. extractionextract with an aqueous 1 M hydrochloric acid solution
  9. dry with materiala saturated aqueous sodium bicarbonate solution, dry the organic layer over Na2SO4
  10. filtrationfilter
  11. customevaporate in vacuo
  12. customto give a residue
  13. extractionextract with a saturated aqueous sodium thiosulfate solution
  14. dry with materialdry the over Na2SO4
  15. filtrationfilter
  16. customevaporate in vacuo
  17. customto give a residue
  18. additioncontaining fractions
  19. customevaporate

Sources & evidence

ORD record
ord-0bcc6c62742a4ff5a1f6394254b98f33
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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