Pyridine → 5,6-Bis(nitrooxy)hexyl 4-nitrophenyl carbonate

HRID 1643423Notes

Reaction equation

HRID 1643423 reaction equation
[N+:1]([O-:15])([O:3][CH2:4][CH:5]([O:11][N+:12]([O-:14])=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][OH:10])=[O:2].Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:18].N1C=CC=CC=1>C(Cl)Cl.O>[C:17](=[O:18])([O:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)[O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([O:11][N+:12]([O-:14])=[O:13])[CH2:4][O:3][N+:1]([O-:15])=[O:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 579416215,6-Bis(nitrooxy)hexan-1-ol

Product 1

HCID 866386565,6-Bis(nitrooxy)hexyl 4-nitrophenyl carbonateYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of 6-hydroxyhexane-1,2-diyl dinitrate (150 mg, 0.67 mmol) in CH2Cl2 (15 mL) at rt was added 4-nitrophenyl chloroformate (202 mg, 1.00 mmol) and followed by pyridine (159 mg, 2.01 mmol). The mixture was stirred at rt over night and diluted with H2O. The mixture was extracted with CH2Cl2 and the organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1; column 25M; TLC method: n-hexane/ethyl acetate 7/3; Rf=0.35), affording product (210 mg, yield 81%).

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (Biotage SP1; column 25M; TLC method: n-hexane/ethyl acetate 7/3; Rf=0.35)

Sources & evidence

ORD record
ord-e5c9c085d2924544a2fb15007ba94392
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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