Triphenylphosphine → Ethyl 3-{4-[3-(3,4-dichlorophenyl)propoxy]phenyl}-3-ethoxypropionate

HRID 1515083

Reaktionsgleichung

Reaktionsgleichung von HRID 1515083
[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].[Cl:18][C:19]1[CH:20]=[C:21]([CH2:26][CH2:27][CH2:28]O)[CH:22]=[CH:23][C:24]=1[Cl:25].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>[Cl:18][C:19]1[CH:20]=[C:21]([CH2:26][CH2:27][CH2:28][O:17][C:14]2[CH:13]=[CH:12][C:11]([CH:4]([O:3][CH2:1][CH3:2])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:16][CH:15]=2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 190753133-(3,4-Dichlorophenyl)propan-1-ol2×HCID 66777355Diethylazodicarboxylate tolueneHCID 67058135Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate

Produkt 1

HCID 67058188Ethyl 3-{4-[3-(3,4-dichlorophenyl)propoxy]phenyl}-3-ethoxypropionateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate (100 mg, 0.420 mmol) produced in Example 1 (1C) and 3-(3,4-dichlorophenyl)propanol (129 mg, 0.630 mmol) synthesized in (11A) were dissolved in tetrahydrofuran (10 mL), and triphenylphosphine (178 mg, 0.680 mmol) and a 40% diethyl azodicarboxylate toluene solution (309 μL, 0.680 mmol) were added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 50° C. for 4 hours. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (130 mg, yield: 73%).

Aufarbeitung

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound
  4. customwas obtained as a colorless oily substance (130 mg, yield: 73%)

Quellen und Nachweise

ORD-Eintrag
ord-5d20314ba4d54297a24e199902750b6d
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222281B2

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