Triphenylphosphine → HCID 19423911, compound

HRID 743333Notes

Reaction equation

HRID 743333 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][OH:7])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:27]1([CH2:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][O:7][C:41]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:35][CH2:34][CH2:33][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 766463-(Dimethylamino)-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 572468HCID 572468, compound

Product 1

HCID 19423911HCID 19423911, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

134 mg of 3-(N,N-dimethylamino)propanol and 342 mg of triphenyl phosphine were added to a solution of 230 mg of 2-(3-phenylpropyl)phenol (prepared as described in Preparation 29) in 10 ml of methylene chloride, and the mixture was cooled with ice and stirred. 227 mg of diethyl azodicarboxylate were then added dropwise to the solution, and the mixture was stirred at room temperature for 5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and ethyl acetate and water were added to the residue and shaken. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 115 mg (yield 36%) of the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was cooled with ice
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure, and ethyl acetate and water
  4. additionwere added to the residue
  5. stirringshaken
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was then removed by distillation under reduced pressure
  9. customthe resulting residue was purified by column chromatography through silica gel
  10. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-0947e3ec2eea4ecdacb9bac1969f3a13
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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