Water → 2,6-Diisopropyl-3-hydroxymethyl-4-(4fluorophenyl)-5-(2-propenyl)-pyridine

HRID 324822

Reaktionsgleichung

Reaktionsgleichung von HRID 324822
C[O:2][C:3]([C:5]1[C:6]([CH:24]([CH3:26])[CH3:25])=[N:7][C:8]([CH:21]([CH3:23])[CH3:22])=[C:9]([CH2:18][CH:19]=O)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O.O.[C:28](OCC)(=O)C.CCCCCC>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:24]([C:6]1[C:5]([CH2:3][OH:2])=[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:9]([CH2:18][CH:19]=[CH2:28])=[C:8]([CH:21]([CH3:22])[CH3:23])[N:7]=1)([CH3:25])[CH3:26]

Komponenten

5

Edukt 3

HCID 962WaterHCID 21226206Ethyl acetate hexaneHCID 22005171Methyl-2,6-diisopropyl-4-(4-fluorophenyl)-5-(2-oxoethyl)-3-pyridinecarboxylate

Produkt 1

HCID 220052812,6-Diisopropyl-3-hydroxymethyl-4-(4fluorophenyl)-5-(2-propenyl)-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74505Methyltriphenyliphosphonium bromideKatalysator

Versuchsvorschrift

The title compound was prepared from methyl-2,6-diisopropyl-4-(4-fluorophenyl)-5-(2-oxoethyl)-3-pyridinecarboxylate (Example 82, Step A) and methyl triphenylphosphonium bromide according to the procedures described in Example 1, Steps F-H. 1H NMR (300 MHz, CDCl3): δ 7.13 (m, 4 H), 5.73 (m, 1H) 4.81 (dd, J=4.8, 1.8 Hz, 2 H), 4.35 (s, 2 H), 3.43 (septet, J=6.6 Hz, 1 H), 3.21 (septet, J =6.6 Hz, 1 H), 3.07 (d, J=1.8 Hz, 2 H), 1.24 (m, 13 H). FAB-MS: calcd for (C21H26FNO) 327, found 328 (M+H). Anal. Calcd for C21H26FNO: C, 74.17; H, 7.71; N, 4.12; F, 5.59+0.7 H2O. Found: C, 74.17; H, 7.57; N, 3.94; F, 5.26. mp 69-71° C. Rf=0.35 (15% ethyl acetate/hexane).

Quellen und Nachweise

ORD-Eintrag
ord-648c200873f6454f89a1bd919f902973
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218431B1

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