Dimethyl Sulfoxide → 3-[3-(1,1-Dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropionaldehyde

Participants

Reaction Steps

To a solution of oxalyl chloride (461 mg, 3.6 mmol) in CH2Cl2 (10 mls) at -78° C. was added dimethylsulfoxide (600 mg, 7.68 mmol) dropwise and the resulting mixture was stirred for 5 mins. A solution of 3-[3-(1,1-dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2yl]-2,2-dimethylpropanol (1.81 g, 3.2 mmol) in CH2Cl2 (5 mls) was then added dropwise and the reaction was stirred for 20 mins at -78° C. Triethylamine (1,62 g, 16.0 mmol) was then added dropwise, the cooling bath was withdrawn and the reaction allowed to warm to r.t. It was then diluted with aqueous sat'd NaHCO3 (20 mls) and the layers were separated. The aqueous was extracted with CH2Cl2 (2×20 mls). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 1:1) to afford 1.58 g (86%) of 3-[3-(1,1-dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropionaldehyde as a lemon yellow solid.

Provenance & Evidence