Water → HCID 59590766, compound

Temperature

-78 °C

At −78° C., lithium bis(trimethylsilyl)amide (1.0 M in hexanes) (4 mL, 26 mmol) was added slowly to a solution of methyl 2-(trimethylsilyl)acetate (4 g, 26 mmol) in THF (20 mL). The reaction mixture was maintained at −78° C. for 22 minutes. 1.2 (3.5 g, 15 mmol) in THF (20 mL) was then added slowly to the mixture. The mixture was stirred at −78° C. and allowed to warm to room temperature overnight. The reaction mixture was then poured into water (30 mL) and extracted with EtOAc (300 mL). The organic layers were washed with brine and dried over anhydrous sodium sulfate. After removing solvent by rotary evaporation, the residue was purified by column chromatography (1:4 EtOAc/hexane). The Product 1.3 was obtained in 38% yield as a white solid.

1. temperatureto warm to room temperature overnight
2. extractionextracted with EtOAc (300 mL)
3. washThe organic layers were washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. customAfter removing solvent
6. customby rotary evaporation
7. customthe residue was purified by column chromatography (1:4 EtOAc/hexane)

ORD record

ord-f0ac1a24674a4d7eae998ba7935f8d8a

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450522B2