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Triphenylphosphine → 2-(2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpyrrolidine

HRID 743246
Notes
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Reaction equation

HRID 743246 reaction equation
N(C(OCC)=O)=NC(O[CH2:6][CH3:7])=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[CH:18]=[CH:19][CH:20]=1.CC(O)[CH2:32][N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:6][CH2:7][CH:37]2[CH2:36][CH2:35][CH2:34][N:33]2[CH3:32])[CH:18]=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 99015alpha-Methyl-1-pyrrolidineethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 105854482-(2-(3-Methoxyphenyl)ethyl)phenol

Product 1

HCID 158968632-(2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpyrrolidineYield 36.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.3 g of diethyl azodicarboxylate were added dropwise, whilst ice-cooling and stirring, to a solution of 10.6 g of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 20), 8.4 g of 1-methyl-2-pyrrolidylethanol and 17 g of triphenylphosphine in 200 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 15 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. 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 5.70 g (yield 36%) of the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  3. customthe resulting residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by column chromatography through silica gel
  7. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-9a95b98c04ac46c3bc8556384de957ca
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05556864

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes