2-Chloro-N-methoxy-N-methylacetamide → HCID 86708713, compound

Participants

Reaction Steps

To a solution of (6-bromonaphthalen-1-yloxy)triisopropylsilane (10.4 g, 27.5 mmol) in tetrahydrofuran (180 mL) under argon at −78° C. was added n-butyllithium (2.5M in hexanes, 11.5 mL, 28.7 mmol). After stirring at this temperature for one hour, a solution of 2-chloro-N-methoxy-N-methyl acetamide (7.6 g, 55.2 mmol) in tetrahydrofuran (10 mL) was added to the reaction via cannula. The dry ice bath was removed and the reaction was allowed to warm to room temperature. After one hour at room temperature the reaction was diluted with ethyl acetate and the organics were washed with saturated aqueous NH4Cl solution, water and brine. The organic layer was dried (MgSO4) and concentrated, and the resulting residue was purified by flash chromatography to yield 2-chloro-1-(5-(triisopropylsilyloxy)-naphthalen-2-yl)ethanone (7.8 g, 75%) as a pale yellow oil.

Provenance & Evidence