Tetrahydrofuran → 3-Hydroxy-3-[4-(spiro[5.5]undec-1-en-2-ylmethoxy)-phenyl]-propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl acetate (2.2 mL) in tetrahydrofuran (100 mL) was added dropwise a 2M heptane/tetrahydrofuran/ethylbenzene solution of lithium diisopropylamide (11.25 mL) at −78° C. under argon atmosphere over 15 minutes, followed by stirring the reaction mixture at −78° C. for 30 minutes. Then, to the reaction mixture was added dropwise a solution of 4-(spiro[5.5]undec-1-en-2-ylmethoxy)-benzaldehyde (4.27 g) obtained in Step 6 in tetrahydrofuran (15 mL) over 10 minutes, followed by stirring the reaction mixture at −78° C. for 40 minutes. After the temperature was raised to room temperature, saturated aqueous ammonium chloride solution (100 mL) was added carefully to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:4 to 1:3) to give 3-hydroxy-3-[4-(spiro[5.5]undec-1-en-2-ylmethoxy)-phenyl]-propionic acid ethyl ester (4.98 g).

Provenance & Evidence