Tetrahydrofuran → Ethyl acetate methanol ammonium hydroxide
Reaction equation
C(C1C=C(C=CC=1CN1CCCC1)CC1C2C=CC(O)=CC=2SC=1C1C=C[C:15]([O:18][CH2:19][CH2:20]N2CCCC2)=[CH:14]C=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1C[O:49][CH2:48]C1>>[NH4+:2].[OH-:18].[CH3:48][OH:49].[CH3:20][CH2:19][O:18][C:15]([CH3:14])=[O:49]Participants
4
Procedure
To 3-[3-cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]-thiophene (29 mg, 0.054 mmol) in THF (2 mL) at 0° C. under argon was added lithium aluminum hydride (14 mg) in one portion. The resulting mixture was allowed to stir at ambient temperature for 7 h before quenching with water (2 mL) and 1.0M sodium hydroxide (1 mL). The stirring was continued for 30 min. The mixture was further diluted with brine (50 mL) and extracted with dichloromethane (50 mL×3). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with NH4OH:MeOH:EtOAc (5:10:85) afforded the product (7 mg, 24%).