Ethyl trimethylsilylacetate → HCID 68814611, compound

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence