Tetrahydrofuran → 5-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridine

HRID 1966248Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1[CH2:35][O:34][CH2:33][CH2:32]1>>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:32][CH2:33][O:34][CH3:35])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran2×

HCID 11776Triphenylphosphine

HCID 187656985-Chloro-2-nitropyridin-3-ol

Product 1

HCID 674861005-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridineYield 90%

Procedure

5-Chloro-2-nitro-pyridine-3-ol (86 mmol) is dissolved in THF (300 ml) and triphenylphosphin (2 eq.) and ethyleneglycolmonomethylether (1 eq.) is added at 0° C. After addition of di-tert.-butylazodicarboxylate (2 eq) in THF (100 ml), the reaction is stirred five hours at room temperature. The solvent is removed in vacuo. 5-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridine is obtained after column chromatography (heptane/ethyl acetate) as yellow solid in a yield of 90%. HPLC (method C): 1.59 min; LC-MS (method A): 1.47 min, 233.1 (MH+).

Workup

customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-c00e04f2a68f488887bd704d07822884
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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