Triphenylphosphine → Ethyl 6-[4-({[3-[(2,6-dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylate

HRID 646016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646016
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]1[C:14]([CH2:15][OH:16])=[C:13]([CH:17]([CH3:19])[CH3:18])[O:12][N:11]=1.O[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[C:33]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32][CH:31]=[CH:30]3)=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]1[C:14]([CH2:15][O:16][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][CH:36]=3)[C:33]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32][CH:31]=[CH:30]4)=[CH:25][CH:26]=2)=[C:13]([CH:17]([CH3:19])[CH3:18])[O:12][N:11]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59264856Ethyl 6-(4-hydroxyphenyl)-1-naphthalenecarboxylateHCID 59264881[3-[(2,6-Dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolyl]methanol

Produkt 1

HCID 59264872Ethyl 6-[4-({[3-[(2,6-dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylateAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of [3-[(2,6-dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolyl]methanol (0.105 g, 0.35 mmol), ethyl 6-(4-hydroxyphenyl)-1-naphthalenecarboxylate (0.102 g, 0.35 mmol), triphenylphosphine (0.092 g, 0.35 mmol) and diisopropyl azodicarboxylate (0.063 mL, 0.35 mmol) in toluene (3.5 mL) was placed in microwave reaction tube and heated to 80° C. for 500 seconds. The solution was concentrated and purified by chromatography (silica gel, hexane to 1:4 ethyl acetate: hexanes) to provide the title compound (0.126 g, 60.9% as 0.2 EtOAc). 1H NMR (DMSO-d6): δ 8.79 (d, J=9 Hz, 1H), 8.28 (d, J=2 Hz, 1H), 8.23 (d, J=8 Hz, 1H), 8.09 (d, J=7 Hz, 1H), 7.98 (dd, J=2, 9 Hz, 1H), 7.81 (d, J=9 Hz, 2H), 7.61 (t, J=8 Hz, 1H), 7.46 (d, J=8 Hz, 2H), 7.32 (t, J=8 Hz, 1H), 7.16 (d, J=9 Hz, 2H), 5.08 (s, 2 H), 4.40 (q, J=7 Hz, 2 H), 4.29 (s, 2 H), 3.34 (septet, J=7 Hz, overlapping H2O 1 H), 1.37 (t, J=7 Hz, 3 H), 1.22 (d, J=7 Hz, 6 H). ESI-LCMS m/z 574 (M+H)+.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. custompurified by chromatography (silica gel, hexane to 1:4 ethyl acetate: hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c2733fba50f54f45a9518c20857d1819
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705028B2

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