Lithium Hexamethyldisilazide → HCID 69313656, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2,4-dichlorophenylacetate (2 g) in anh. THF (27 mL), at −78° C., under N2, a 1M solution of LHMDS in THF (10.04 mL) was added dropwise and the mixture was stirred at −78° C. for 30 min. Neat intermediate 20 (2.87 g, 1.3 eq) was then added dropwise at −78° C. and the dropping funnel was washed with anh. THF (2 mL). The cooling bath was then removed and the mixture was stirred at r.t. for 3.5 hr. The solvents were evaporated under reduced pressure. The residue was dissolved in ether, washed with water (3×30 mL) and brine (1×30 mL) and dried over anh. Na2SO4. The solids were filtered and the solvent evaporated. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 9:1) to give the title compound as a pale yellow oil (2.7 g).

Provenance & Evidence