Chlorotrimethylsilane → HCID 58292634, compound

Temperature

55 °C

To a mixture of zinc powder (0.65 g, 10.0 mmol) in anhydrous THF (15 mL) was added TMSCl (0.13 mL, 1.0 mmol) at 40° C. The resulting mixture was stirred at 55° C. for 15 min and cooled to 37° C., followed by addition of ethyl 2-bromoacetate (0.45 mL, 4.0 mmol). The reaction mixture was stirred at this temperature for an additional 30 min. To the solution of 2,4-dimethoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde (0.29 g, 1.0 mmol) in anhydrous THF (20 mL) cooled at −78° C., was added above prepared solution dropwise. The reaction mixture was allowed to stir at room temperature for 1.5 hr and quenched by aqueous ammonium chloride (20 mL). The reaction mixture was extracted with ethyl acetate (2×15 mL), the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/PE=1/3) on silica gel to give the title compound as a white solid. (110 mg, Yield: 39.3%). MS (ESI) m/z=281 [M+H]+.

1. temperaturecooled to 37° C.
2. stirringThe reaction mixture was stirred at this temperature for an additional 30 min
3. additionwas added
4. customabove prepared solution dropwise
5. stirringto stir at room temperature for 1.5 hr
6. customquenched by aqueous ammonium chloride (20 mL)
7. extractionThe reaction mixture was extracted with ethyl acetate (2×15 mL)
8. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
9. concentrationconcentrated in vacuo
10. customThe residue was purified by column chromatography (EtOAc/PE=1/3) on silica gel

ORD record

ord-8f85760ef19143e4afb79408d3612acc

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343944B2