Tetrahydrofuran → HCID 131734940, compound

Participants

Reaction Conditions

Reaction Steps

Tert-butyl (2-chloro-5-cyano-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (864 mg, 2.282 mmol), (2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) chloride (84 mg, 0.114 mmol), and potassium phosphate, dibasic (1192 mg, 6.85 mmol) were added to a 100 ml flask, and the flask was purged with N2. 3-bromobut-3-en-1-ol (0.226 mL, 2.282 mmol) and THF (12 mL) were added, followed by water (2.182 mL). The reaction was heated at 60° C. for 1 h. The reaction was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water, then brine, dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0-50% EtOAc/Hex; 120 g column). Tert-butyl (2-chloro-5-cyano-3-(4-hydroxybut-1-en-2-yl)phenyl)carbamate (317 mg) was obtained as a colorless glass.

Provenance & Evidence