Cyclohexanol → HCID 58495607, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere add 6-chloro-pyridin-3-ol (2.5 g, 19.3 mmol), cyclohexanol (1.93 g, 19.3 mmol), tri-n-butylphosphine (5.07 g, 25.1 mmol), and ADDP (6.32 g, 25.1 mmol) to benzene (100 mL) and THF (10 mL) at 0° C. Stir the mixture at 0° C. for 1 h and at room temperature for 12 h. Dilute with EtOAc and water. Separate the layers and extract the aqueous layer with EtOAc. Wash the organic phase with water (30 mL) and brine (20 mL). Dry the organic phase over Na2SO4, filter, and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (400 g) eluting with hexane/EtOAc (1:0 to 98:2 gradient) to obtain the desired intermediate as clear oil (1.8 g, 58%). MS (APCI+) m/z: 212 (M+H)+.

Provenance & Evidence