1,1-Dichloroethane → (5R)-1-chloro-5,6-bis(nitrooxy)hexyl propionate

HRID 1361924Notes

Reaction equation

HRID 1361924 reaction equation
[Cl:1]C(Cl)C.[N+:5]([O-:19])([O:7][CH2:8][C@H:9]([O:15][N+:16]([O-:18])=[O:17])[CH2:10][CH2:11][CH2:12][CH:13]=[O:14])=[O:6].[C:20](Cl)(=[O:23])[CH2:21][CH3:22].C(=O)(O)[O-].[Na+]>[Cl-].[Zn+2].[Cl-]>[C:20]([O:14][CH:13]([Cl:1])[CH2:12][CH2:11][CH2:10][C@@H:9]([O:15][N+:16]([O-:18])=[O:17])[CH2:8][O:7][N+:5]([O-:19])=[O:6])(=[O:23])[CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 86622539(2R)-6-oxohexane-1,2-diyl dinitrate

Product 1

HCID 86622540(5R)-1-chloro-5,6-bis(nitrooxy)hexyl propionate

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Zinc chloride (1.3 g, 9.54 mmol) was added to a dichloroethane (11.9 mL) solution of (2R)-6-oxohexane-1,2-diyl dinitrate (530 mg, 2.39 mmol) and propionyl chloride (0.23 mL, 2.62 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 2 hours. Saturated aqueous sodium bicarbonate was added, and the solution was extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica eluting with ethyl acetate/hexanes afforded the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 6.47 (d, J=5.0 Hz, 1H), 5.34-5.28 (m, 1H), 4.77 (dd, J=13.0, 3.5 Hz, 1H), 4.51 (dd, J=13.0, 6.5 Hz, 1H), 2.41 (q, J=7.5 Hz, 2H), 2.08 (q, J=7.5 Hz, 2H), 1.87-1.78 (m, 2H), 1.78-1.60 (m, 2H), 1.18 (t, J=7.5 Hz, 3H).

Workup

  1. extractionthe solution was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e9542366a9cb4c0e97f9e5d3e801577b
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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