Water → 4-[4-[6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanol Oxalate

Participants

Reaction Conditions

Reaction Steps

4-[6-Benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenol (0.10 g; 0.19 mmol), 4-chlorobutyric acid methyl ester (27 mL; 0.22 mmol) and Cs2CO3 (0.43 g; 1.31 mmol) were combined in 2 mL of DMF and heated in an oil bath maintained at 80° C. for 3 h. After cooling to room temperature, water (30 mL) was added, and extraction was carried out with EtOAc (4×25 mL). The combined organics were washed with brine and dried by passage through Na2SO4. Purification was effected by flash chromatography on silica gel, eluting with EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%). The title product was obtained as a colorless oil (92 mg, 78%).

Provenance & Evidence