Hydrogen Peroxide → HCID 86721097, compound

Participants

Reaction Steps

A solution of 1 M allylbis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane in pentane in anhydrous THF (10 mL) was cooled to −78° C. To the solution was added 4-chloro-3-fluoropicolinaldehyde (0.5 g, 3.13 mmol) in 10 mL of THF dropwise for 20 min. The resulting solution was stirred for additional 1 h. To the mixture was added MeOH (1 mL), followed addition of lithium hydroxide (0.300 g, 12.54 mmol), hydrogen peroxide (0.384 mL, 12.54 mmol) and 10 mL of 1 N NaOH. The content was allowed to warm up to rt and stirred for 1 h. The reaction mixture was diluted with EtOAc, washed with brine (2×20 mL), dried over Na2SO4, concentrated and purified by silica gel chromatography to provide (R)-1-(4-chloro-3-fluoropyridin-2-yl)but-3-en-1-ol (0.54 g, 85%). MS (ESI) m/z: 202.1 (M+H)+.

Provenance & Evidence