Reaktion #426777

ord-34e4cacbf17f4b96a7d239c465bd181b

Reaktionsgleichung

CC(C)(C)[Si](C)(C)OCCOc1cc([N+](=O)[O-])ccc1C=O
2-([2-tert-butyldimethylsiloxy]ethoxy)-4-nitrobenzaldehyde
[H-].[Na+]
sodium hydride
CCCCCC.CCOC(C)=O
EtOAc Hexane
CCOP(=O)(Cc1ccc(-c2cn3cc(C)ccc3n2)cc1)OCC
diethyl [4-(6-methylimidazo[1,2-a]pyridin-2-yl)benzyl]phosphonate
→
Cc1ccc2nc(-c3ccc(/C=C/c4ccc([N+](=O)[O-])cc4OCCO[Si](C)(C)C(C)(C)C)cc3)cn2c1
title compound
Ausbeute 64.3%
Cc1ccc2nc(-c3ccc(/C=C/c4ccc([N+](=O)[O-])cc4OCCO[Si](C)(C)C(C)(C)C)cc3)cn2c1
6-Methyl-2-(4-{(E)-2-[4-nitro-2-(2-tert-butyldimethylsiloxyethoxy)phenyl]ethenyl}phenyl)imidazo[1,2-a]pyridine
Ausbeute 64.3%

Edukte

CC(C)(C)[Si](C)(C)OCCOc1cc([N+](=O)[O-])ccc1C=O
2-([2-tert-butyldimethylsiloxy]ethoxy)-4-nitrobenzaldehyde
—
Alkene
[H-].[Na+]
sodium hydride
CCCCCC.CCOC(C)=O
EtOAc Hexane
CCOP(=O)(Cc1ccc(-c2cn3cc(C)ccc3n2)cc1)OCC
diethyl [4-(6-methylimidazo[1,2-a]pyridin-2-yl)benzyl]phosphonate

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePrepared

Vorschrift

Prepared as described in the Alkene Formation section using sodium hydride (40 mg, 60% dispersion in mineral oil, 1.00 mmol), diethyl [4-(6-methylimidazo[1,2-a]pyridin-2-yl)benzyl]phosphonate (0.300 g, 0.837 mmol) and 2-([2-tert-butyldimethylsiloxy]ethoxy)-4-nitrobenzaldehyde (0.272 g, 0.837 mmol) in dry THF (30 ml) to give the title compound (0.285 g, 64%) as an orange solid after work-up and flash chromatography (2:1 EtOAc/Hexane).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08895313B2uspto-grants-2014_11