Dimethyl Sulfoxide → 4-(2-tert-Butyl-5-nitro-phenyl)-but-3-enal

Participants

Reaction Conditions

Reaction Steps

4-(2-tert-Butyl-5-nitro-phenyl)-but-3-en-1-ol (1.024 g) was dissolved in 10 ml of CH2Cl2 and added dropwise over 5 min to a −78 C mix of oxalyl chloride (0.645 ml), DMSO (0.583 ml), and 10 ml CH2Cl2. The reaction was stirred at −78 C for 1 h, then treated with a solution of TEA (1.52 ml) in 7 ml CH2Cl2 and stirred at −78 C for an additional 25 min, then warmed to −30° C. for 35 min. The reaction was treated with 50 ml of saturated aqueous NH4Cl, diluted with H2O and extracted with EtOAc. The organic layer was brine-washed, dried over Na2SO4, filtered, and concentrated in vacuo to yield a yellow oil which was used as is in Preparation LXXXVIII.

Provenance & Evidence