Carbon tetrabromide → HCID 59299959, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (6-benzyloxy-5-propoxy-pyridin-2-yl)-methanol (1.09 g, 4.0 mmole) and 20 mL of N,N-dimethylformamide stirred and cooled with an ice bath to 0° C. is added triphenylphosphine (1.57 g, 6.0 mmole) followed by carbon tetrabromide (1.99 g, 6.0 mmole). This is stirred for 15 minutes maintaining temperature between 0-5°. Sodium azide is then added (781 mg, 12.0 mmole) and the reaction mixture stirred for 24 hrs at ambient temperature. The reaction mixture is diluted with water and extracted with ether. The combined extracts were dried over sodium sulfate, filtered, evaporated and the residue chromatographed on silica gel eluting with hexane/ethyl acetate to give a-clear liquid, 1.05 g, (88%); MS (ES+): m/z 299.1 (M+H).

Provenance & Evidence