4-Methylpyridine → 4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)-2-hydroxyethyl]pyridine

HRID 921

Reaktionsgleichung

Reaktionsgleichung von HRID 921
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH3:13][CH2:14][O:15][C:16]([CH3:18])=O.[CH3:19][CH2:20][CH2:21]CCC.N1C=CC=CC=1.[H][H].C[CH2:34][O:35]C(C)=O.[CH3:39][OH:40]>N1C=CC=CC=1>[CH:14]1([O:15][C:16]2[CH:18]=[C:8]([CH:39]([OH:40])[CH2:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[CH:9]=[CH:10][C:11]=2[O:35][CH3:34])[CH2:21][CH2:20][CH2:19][CH2:13]1

Komponenten

7

Edukt 5

HCID 79634-MethylpyridineHCID 21226206Ethyl acetate hexaneHCID 21584119Ethylacetate methanolHCID 178418339ButyllithiumHCID 178418478HCID 178418478, Verbindung

Produkt 1

HCID 221458574-[2-(3-Cyclopentyloxy-4-methoxyphenyl)-2-hydroxyethyl]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

From 4-methylpyridine (3.00 g, 32.1 mmol); n-butyllithium (32.1 mmol), and Intermediate 1 (6.82 g, 31.0 mmol). The crude product was subject to chromatography [SiO2 ; EtOAc-hexane, 3:2 (500 ml) to 4:1 (1000 ml) then EtOAc-methanol 9:1 (1500 ml)] to afford the title compound (9.68 g) as fine white needles m.p. 97°-101° C. (from toluene) δH (CDCl3) 1.5-2.0 (SH, br m, (CH2)4, 2.45(1H, br, s, CHOH), 2.96 (2H, d, J 6.5 Hz, CH2 pyridine), 3.80 (3H, s, OMe), 4.70 (1H, br, m, OCHCH2), 4.81 (1H, t, J 6.5 Hz, CHOH), 6.76 (3H, s, ArH ortho to OMe+2×ArH meta to OMe), 7.00 (2H, dm, J 4.5 Hz, pyridine H3, H5), and 8.33 (2H, dm, J 4.5 Hz, pyridine H2, H6).

Quellen und Nachweise

ORD-Eintrag
ord-346c438e3d4843a0b0aa5ffa14cf7153
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723460

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