Lithium Hexamethyldisilazide → HCID 69313656, compound

Temperature

-78 °C

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).

1. washthe dropping funnel was washed with anh. THF (2 mL)
2. customThe cooling bath was then removed
3. stirringthe mixture was stirred at r.t. for 3.5 hr
4. customThe solvents were evaporated under reduced pressure
5. dissolutionThe residue was dissolved in ether
6. washwashed with water (3×30 mL) and brine (1×30 mL)
7. dry with materialdried over anh. Na2SO4
8. filtrationThe solids were filtered
9. customthe solvent evaporated
10. customThe crude product was purified by flash chromatography (silica gel, cHex/EtOAc 9:1)

ORD record

ord-e4191aa082d64a3b9c35364e7a6357d4

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329667B2