Pyridine → (4R,5R)-3-methyl-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate

Participants

Reaction Steps

To a solution of (2R,3R)-6-hydroxy-4-methylhexane-2,3-diyl dinitrate (Intermediate 2, 0.78 g, 3.26 mmol) in CH2Cl2 (15 mL) cooled at 0° C., 1-chloroethyl chloroformate (0.355 mL, 3.26 mmol) was added. Then a solution of Pyridine (0.263 mL, 3.26 mmol) was added dropwise. The solution was stirred at room temperature overnight. Then it was diluted with CH2Cl2 (25 mL) and washed with HCl 1 N (2×15 mL), a saturated solution of NaHCO3 (15 mL) and brine. The organic layer was dried over Na2SO4 and concentrated affording the title compound as colorless oil.

Provenance & Evidence