Ethyl trimethylsilylacetate → HCID 68814611, compound

Temperature

-78 °C

A solution of ethyl (trimethylsilyl)acetate (12.07 g, 75 mmol) in anhydrous THF (60 mL) at −78° C. was treated dropwise with LiHMDS (1M in THF, 66 mL). The resulting mixture was stirred at −78° C. for 30 minutes. A solution of 52.3 (14.0 g, 50 mmol) in THF (10 mL) was added to the mixture over 20 minutes. The resulting mixture was stirred at −78° C. for 2 hours before warming to 0° C. The reaction mixture was quenched with NH4Cl (sat. 200 mL) and extracted with ethyl acetate (70 mL×4). The combined organic layers were washed with saturated brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 30% ethyl acetate in Hexane). [6-(4-Methoxy-benzyloxy)-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-acetic acid (52.4) was obtained as a light yellow oil (12.2 g, 69% yield). MS ESI (pos.) m/e: 353 (M+1)+.

1. stirringThe resulting mixture was stirred at −78° C. for 2 hours
2. temperaturebefore warming to 0° C
3. customThe reaction mixture was quenched with NH4Cl (sat. 200 mL)
4. extractionextracted with ethyl acetate (70 mL×4)
5. washThe combined organic layers were washed with saturated brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography (silica gel, 30% ethyl acetate in Hexane)

ORD record

ord-1060b513d062483eb2a4410ae3203aba

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582803B2