Water → HCID 21706312, compound

Participants

Reaction Conditions

Reaction Steps

4-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenol (0.25 g; 0.58 mmol), 0.21 g (0.70 mmol) of the triisopropylsilyl ether prepared above and Cs2CO3 (1.33 g; 4.07 mmol) were combined in 5 mL of DMF in a flame-dried, argon-filled flask and heated in an oil bath maintained at 70° C. for 2 h. After cooling to room temperature, water was added (25 mL) and extraction was carried out with EtOAc (4×25 mL). The combined organics were dried by passage through Na2SO4. The triisopropylsilyl protecting group was removed by stirring with an excess of tetrabutylammonium fluoride in THF at room temperature for 0.5 h. The product was isolated as a colorless oil (165 mg; 58%) by flash chromatography on silica gel, eluting with EtOAc(10-90%)/Et3N(0-5%)/MeOH(0-5%). Conversion to the oxalate was effected in the usual way.

Provenance & Evidence