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ChemicalBook CAS DataBase List N,N-DIMETHYLHEXANAMIDE

N,N-DIMETHYLHEXANAMIDE synthesis

10synthesis methods
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Yield: 91%

Reaction Conditions:

with C19H26ClIrNOP;potassium tert-butylate in toluene at 80; for 12 h;Schlenk technique;Inert atmosphere;Sealed tube;Green chemistry;

Steps:

2. General procedure for α-alkylation of amides
General procedure: To a 5 mL dried Schlenk tube was added with iridium complex 1b (2.7 mg, 0.5 mol %), KOtBu (134 mg, 1.2 mmol), Benzyl alcohol 2a (103 µL, 1 mmol), and N,N-dimethylacetamide 3a (150 µL, 2.0 mmol) under an argon atmosphere, followed by toluene (1.0 mL). The flask was sealed tightly with a teflon plug under an argon atmosphere, and the solution stirred in a 80 °C oil bath for 12 h. Then the reaction mixture was cooled to room temperature, and the solvent was removed under high vacuum. The residue was dissolved in dichloromethane and filtrated though celite. The filter was collected and the volatiles were removed under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate/petroleum ether (1:4) to afford the product 4a, colorless oil, isolated yield: 92%, 160 mg.

References:

Yao, Wubing;Ma, Xiaochen;Guo, Le;Jia, Xiangqing;Hu, Aiguo;Huang, Zheng [Tetrahedron Letters,2016,vol. 57,# 26,p. 2919 - 2921] Location in patent:supporting information

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