Triphenylphosphine → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(2-[4-(2-hydroxyethan-1-oxy)phenyl]ethynyl)-1,1-(ethylenedioxy)cyclohexane

HRID 343566

Reaktionsgleichung

Reaktionsgleichung von HRID 343566
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH:12]1([O:17][C:18]2[CH:19]=[C:20]([C:26]3([C:36]#[CH:37])[CH2:31][CH2:30][C:29]4([O:35][CH2:34][CH2:33][O:32]4)[CH2:28][CH2:27]3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:16][CH2:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1CCCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]1([O:17][C:18]2[CH:19]=[C:20]([C:26]3([C:36]#[C:37][C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=4)[CH2:31][CH2:30][C:29]4([O:32][CH2:33][CH2:34][O:35]4)[CH2:28][CH2:27]3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH2:16]1

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 35132082-(4-Iodophenoxy)ethanolHCID 110895964-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane

Produkt 1

HCID 541798624-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(2-[4-(2-hydroxyethan-1-oxy)phenyl]ethynyl)-1,1-(ethylenedioxy)cyclohexane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8082PiperidineLösungsmittel

Versuchsvorschrift

A solution of 4-(2-hydroxyethoxy)phenyl iodide (0.059 g, 0.22 mmol), and 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane (0.080 g, 0.22 nmol) in dry piperidine (1 mL) was treated with a mixture of tetrakis(triphenylphosphine)palladium (0.013 g, 0.011 mmol), cuprous iodide (0.0025 g, 0.013 mmol), and triphenylphosphine (crystal), as described above in Example 11. Purification of the crude product by chromatography (silica gel, 1 to 2% methanol in methylene chloride) followed by pumping in vacuo afforded the titled intermediate as a viscous oil. 1H-NMR (400 MHz, CDCl3) δ 7.39 (d, J=9.0 Hz, 2H), 7.24 (d, J=2.1 Hz, 1H), 7.13 (d-d, J=8.3 Hz, J=2.1 Hz, 1H), 6.85 (d, J=8.7, 2H), 6.84 (d, J=8.3 Hz, 1H), 4.81 (p, J=2.0 Hz, 1H), 4.09 (t, J=4.4 Hz, 2H), 4.00 (s, 4H), 3.97 (t, J=4.4 Hz, 2H), 3.84 (s, 3H), 2.3 to 1.5 (m, 21H with H2O).

Aufarbeitung

  1. customPurification of the crude product by chromatography (silica gel, 1 to 2% methanol in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-4b56e8e3b034477b8d9b5cb306c0e014
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861421

Verknüpfte Notizen

Wird geladen…