Dimethyl Sulfoxide → 6-(1,1-Dimethylethyl)-2-pyridinecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of DMSO (0.90 mL, 12.7 mmol) in dichloromethane (10 mL) at −78° C. was treated with oxalyl chloride (3.1 mL, 2 M in dichloromethane) dropwise, stirred for an additional 15 minutes at −78° C., treated with a solution of the product from Example 115E (0.88 g, 5.3 mmol) in dichloromethane (14 mL) over 10 minutes, stirred for 20 minutes, treated dropwise with triethylamine (3.6 mL, 26.1 mmol) at −78° C., stirred for 10 minutes, warmed to 0° C., stirred for an additional 10 minutes, quenched with water and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 5% ethyl acetate in chloroform to give the title compound (0.77 g, 88% yield).

Provenance & Evidence