Triphenylphosphine → Ethyl 3-ethoxy-3-(4-{[3-(1H-pyrrol-1-yl)benzyl]oxy}phenyl)propionate

HRID 1515077Notes

Reaction equation

HRID 1515077 reaction equation
[CH2:1]([O:3][CH:4]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[N:18]1([C:23]2[CH:24]=[C:25]([CH2:29]O)[CH:26]=[CH:27][CH:28]=2)[CH:22]=[CH:21][CH:20]=[CH:19]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([O:3][CH:4]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([N:18]3[CH:22]=[CH:21][CH:20]=[CH:19]3)[CH:24]=2)=[CH:15][CH:16]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2776531[3-(1H-Pyrrol-1-yl)phenyl]methanolHCID 66777355Diethylazodicarboxylate tolueneHCID 67058135Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate

Product 1

HCID 67058083Ethyl 3-ethoxy-3-(4-{[3-(1H-pyrrol-1-yl)benzyl]oxy}phenyl)propionateYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate (100 mg, 0.420 mmol) produced in Example 1 (1C) and 3-(1H-pyrrol-1-yl)phenylmethanol (104 mg, 0.600 mmol) were dissolved in tetrahydrofuran (2 mL), and triphenylphosphine (165 mg, 0.629 mmol) and a diethyl azodicarboxylate toluene solution (2.2 M, 290 μL, 0.638 mmol) were added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. The solvent in the reaction solution was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 90:10 (v/v)), whereby the objective title compound was obtained as a light yellow oily substance (107 mg, yield: 65%).

Workup

  1. distillationThe solvent in the reaction solution was distilled off under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 90:10 (v/v)), whereby the objective title compound
  3. customwas obtained as a light yellow oily substance (107 mg, yield: 65%)

Sources & evidence

ORD record
ord-43f32b0dead04960801a5840a8b0f80c
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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