4-Chlorobenzaldehyde → HCID 86703245, compound

Participants

Reaction Conditions

Reaction Steps

LDA (1.8M, 18.97 mL, 34.2 mmol) was added dropwise to a solution of methyl 1-cyclopropyl-1H-pyrrole-3-carboxylate (Step 240.6) (4.03 g, 24.40 mmol) in THF (80 mL) at −78° C. and the mixture was stirred for 30 min. A solution of 4-chlorobenzaldehyde (3.77 g, 26.8 mmol) in THF (20 mL) was added at −78° C. The mixture was allowed to warm to −50° C. over 2 hrs, quenched with a saturated aqueous solution of ammonium chloride, and taken up in EtOAc/saturated ammonium chloride solution. The aqueous layer was separated and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 4:1) to afford the title compound (6.1 g, 79% yield) as a yellow solid. TLC (hexane/EtOAc 4:1): Rf=0.21.

Provenance & Evidence