Boron trifluoride etherate → Methyl ((1-(((4-chlorophenyl)methyl)thio)-1-(4-(2-quinolinylmethoxy)phenyl)methyl)thio)acetate

Participants

Reaction Conditions

Reaction Steps

At 0° C., BF3 /Et2O (380 μL, 2.3 equiv.) was added to a solution of 4-(2-quinolinylmethoxy)benzaldehyde (Example 1, Step 1, 352 mg, 1.34 mmoles), methyl thioglycolate (130 μL, 1.1 equiv.) and 4-chlorobenzyl mercaptan (195 μL, 1.1 equiv.) in CH2Cl2 (7 mL) and the mixture was stirred at 0° C. an hour and at room temperature 15 minutes. 25% Aqueous NH4OAc was then added at 0° C. and the products were extracted with EtOAc, dried over Na2SO4 and separated by flash chromatography on silica using EtOAc:toluene 2.5:97.5 and 5:95 to yield the title compound.

Provenance & Evidence