Triphenylphosphine → Dimethyl 4-nitro-1-(2-propoxyethyl)-1H-pyrazole-3,5-dicarboxylate

HRID 855606Notes

Reaction equation

N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][O:16][C:17]([C:19]1[C:23]([N+:24]([O-:26])=[O:25])=[C:22]([C:27]([O:29][CH3:30])=[O:28])[NH:21][N:20]=1)=[O:18].[CH2:31]([O:34][CH2:35][CH2:36]O)[CH2:32][CH3:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[N+:24]([C:23]1[C:19]([C:17]([O:16][CH3:15])=[O:18])=[N:20][N:21]([CH2:36][CH2:35][O:34][CH2:31][CH2:32][CH3:33])[C:22]=1[C:27]([O:29][CH3:30])=[O:28])([O-:26])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

Diisopropyl azodicarboxylate (14.2 mL, 70 mmol) was added to an ice-cooled solution of 4-nitro-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester (EP 1241170, prep 10) (15 g, 60 mmol), 2-propoxyethanol (8.2 mL, 70 mmol) and triphenylphosphine (18.9 g, 70 mmol) in tetrahydrofuran (150 mL), and the reaction stirred at 0° C. for 2.5 hours, then allowed to stir at room temperature for a further 18 hours. The reaction was concentrated in vacuo and the residue purified by column chromatography on silica gel using ethyl acetate:pentane as eluant, and then re-columned using dichloromethane as eluant to afford the title compound as a solid, 14 g.

Workup

stirringto stir at room temperature for a further 18 hours
concentrationThe reaction was concentrated in vacuo
customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-4af92c2d997b4c3386cea044bf288bfb
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262192B2

Reaction notes

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