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Water → 7-(2-Methyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)heptan-1-one

HRID 913056
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 913056
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[N:12]=[CH:13][N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=1.[Li]CCCC.CON(C)[C:32](=[O:45])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]1([CH3:44])[O:43][CH2:42][CH2:41][O:40]1.O>C1COCC1.CCCCCC>[CH3:44][C:39]1([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][C:32]([C:13]2[N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[N:12]=2)=[O:45])[O:40][CH2:41][CH2:42][O:43]1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 673822734-(2-Naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazoleHCID 86645337N-methoxy-N-methyl-7-(2-methyl-1,3-dioxolan-2-yl)heptanamideHCID 178418339Butyllithium

Produkt 1

HCID 673819037-(2-Methyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)heptan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of E2 (1.0 eq.) in THF (0.1 M solution) at −78° C. was added a solution of n-BuLi (1.3 eq.) in hexane. The solution was stirred for 30 min and then a solution of N-methoxy-N-methyl-7-(2-methyl-1,3-dioxolan-2-yl)heptanamide (1.5 eq.) in THF was slowly added. The reaction mixture was stirred for 1 hr at −78° C. and then 1 hr at RT. Then water was added and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried (MgSO4) and the solvent was removed under reduced pressure. The crude was purified by column chromatography on silica gel eluting with 20-50% EtOAc/petroleum ether to obtain E3 as yellow solid. 1H NMR (300 MHz, CDCl3) δ: 8.32 (1H, s), 7.96-7.81 (4H, m), 7.68 (1H, s) 7.53-7.42 (2H, m), 5.85 (2H, s), 3.92 (4H, s), 3.64 (2H, t, J=8.2 Hz), 3.26 (2H, t, J=8.2 Hz), 1.77 (2H, m), 1.69-1.36 (8H, m), 1.31 (3H, s), 0.97 (2H, t, J=8.2 Hz), 0.19 (9H, s). MS (ES) C30H42N2O4Si requires: 522, found: 523 (M+H)+.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 1 hr at −78° C.
  2. custom1 hr
  3. customat RT
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe crude was purified by column chromatography on silica gel eluting with 20-50% EtOAc/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-57181833e29c4f529f880cba0a321863
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08026265B2

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