Reaktionsgleichung
[F-].[K+].CNCCNC.I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].[CH3:17]/[C:18](/[O:24][Si](C)(C)C)=[N:19]\[Si](C)(C)C>[Cu]I.C1(C)C=CC=CC=1>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:19][C:18](=[O:24])[CH3:17]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), KF (350 mg, 6.0 mmol), evacuated, backfilled with Ar. N,N′-Dimethylethylenediamine (11 μL, 0.10 mmol, 10 mol %), 2-iodotoluene (128 μL, 1.01 mmol), N,O-bis(trimethylsilyl)acetamide (300 μL, 1.21 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 16 h. The resulting suspension was allowed to reach room temperature and then filtered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate (20 mL). The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 1:4; 15 mL fractions). Fractions 10–17 provided 78 mg (52% yield) of N-(2-methylphenyl)acetamide as white needles.
Aufarbeitung
- customevacuated
- customThe Schlenk tube was sealed with a Teflon valve
- customto reach room temperature
- filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate (20 mL)
- concentrationThe filtrate was concentrated
- customthe residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 1:4; 15 mL fractions)
Quellen und Nachweise
- ORD-Eintrag
- ord-febe0008a48240be8f190a7b69282a9a
- Quelldatensatz
- uspto-grants-2006_10
- Patentnummer
- US07115784B2
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