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

HRID 889516Notes

Reaction equation

HRID 889516 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].[N+:8]([O-:22])([O:10][C@@H:11]([C@H:13]([O:18][N+:19]([O-:21])=[O:20])[CH2:14][CH2:15][CH2:16][OH:17])[CH3:12])=[O:9].N1C=CC=CC=1>ClCCl>[C:2](=[O:3])([O:4][CH:5]([Cl:7])[CH3:6])[O:17][CH2:16][CH2:15][CH2:14][C@@H:13]([O:18][N+:19]([O-:21])=[O:20])[C@H:11]([O:10][N+:8]([O-:22])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5213051-Chloroethyl chloroformateHCID 59549893(2R,3R)-6-hydroxyhexane-2,3-diyl dinitrate2×

Product 1

HCID 86647015(4R,5R)-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (1.55 mL, 14.2 mmol) was added dropwise to a stirred dichloromethane (50 mL) solution of (2R,3R)-6-hydroxyhexane-2,3-diyl dinitrate (intermediate 1, 2.60 g, 11.6 mmol), followed by pyridine (1.20 mL, 14.8 mmol). After 16 hours, the reaction mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel, eluting with 5-25% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 6.41 (q, J=5.7 Hz, 1H), 5.18-5.28 (m, 2H), 4.18-4.32 (m, 2H), 1.83 (d, J=5.7 Hz, 3H), 1.68-1.90 (m, 4H), 1.42 (d, J=6.4 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel
  3. washeluting with 5-25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-171fb60d92e94dba93c54a2466741970
Source dataset
uspto-grants-2012_08
Patent number
US08252825B2

Reaction notes

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