Allyl bromide → HCID 54079479, compound

HRID 344024Notes

Reaction equation

HRID 344024 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1C[CH2:26][CH2:25][CH2:24]1.C([Li])CCC.C(Br)C=C>C(OCC)(=O)C.CCCCCC>[C:1]([O:5][C:6]([N:8]([CH2:9][CH:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:26][CH:25]=[CH2:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 18787247HCID 18787247, compoundHCID 178418339Butyllithium

Product 1

HCID 54079479HCID 54079479, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine N-t-butoxycarbonyl-2,2-bis-phenyl-ethylamine (2.0 g, 7.73 mmol) and tetrahydrofuran (20 mL) and cool in a dry-ice/acetone bath to -78° C. Slowly, add n-butyllithium (4.4 mL, 1.6M in hexane, 7.04 mmol) and allow to stand for 30 minutes. Add allyl bromide (0.7 mL, 8.09 mmol) maintaining the temperature at -78° C. Warm to ambient temperature and allow to stand for 1.5 hour and then heat to reflux for 5 hours. Cool to ambient temperature and allow to stand for 18 hours. Extract the reaction mixture with a saturated ammonium chloride solution and separate the layers. Extract the aqueous layer with diethyl ether and combine the organic layers. Extract the combine organic layer with water and saturated sodium chloride solution. Separate the organic layer and dry over MgSO4, filter and evaporate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5% ethyl acetate/hexane to give the title compound.

Workup

  1. waitto stand for 1.5 hour
  2. temperatureheat
  3. temperatureto reflux for 5 hours
  4. temperatureCool to ambient temperature
  5. waitto stand for 18 hours
  6. extractionExtract the reaction mixture with a saturated ammonium chloride solution
  7. customseparate the layers
  8. extractionExtract the aqueous layer with diethyl ether
  9. extractionExtract the combine organic layer with water and saturated sodium chloride solution
  10. customSeparate the organic layer
  11. dry with materialdry over MgSO4
  12. filtrationfilter
  13. customevaporate in vacuo
  14. customto obtain a residue

Sources & evidence

ORD record
ord-de1d99e0feee4f97b23426b8a108f27c
Source dataset
uspto-grants-1999_01
Patent number
US05864045

Reaction notes

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