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

HRID 889522Notes

Reaction equation

HRID 889522 reaction equation
[N+:1]([O-:16])([O:3][C@@H:4]([C@H:6]([O:12][N+:13]([O-:15])=[O:14])[CH:7]([CH3:11])[CH2:8][CH2:9][OH:10])[CH3:5])=[O:2].Cl[C:18]([O:20][CH:21]([Cl:23])[CH3:22])=[O:19].N1C=CC=CC=1>C(Cl)Cl>[C:18](=[O:19])([O:20][CH:21]([Cl:23])[CH3:22])[O:10][CH2:9][CH2:8][CH:7]([CH3:11])[C@@H:6]([O:12][N+:13]([O-:15])=[O:14])[C@H:4]([O:3][N+:1]([O-:16])=[O:2])[CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5213051-Chloroethyl chloroformateHCID 59549895(2R,3R)-6-hydroxy-4-methylhexane-2,3-diyl dinitrate2×

Product 1

HCID 86647019(4R,5R)-3-methyl-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  1. washwashed with HCl 1 N (2×15 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-83b3444f692049c1b70625e203e75a77
Source dataset
uspto-grants-2012_08
Patent number
US08252825B2

Reaction notes

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