Methanol → HCID 66609009, compound

HRID 473138Notes

Reaction equation

HRID 473138 reaction equation
[Na].[N+]([C:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7](COCC[Si](C)(C)C)[N:6]=1)([O-])=O.[CH3:21][OH:22]>>[CH3:21][O:22][C:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[NH:7][N:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 86662694HCID 86662694, compound

Product 1

HCID 66609009HCID 66609009, compoundYield 76%

Conditions

Temperature
60 °C

Procedure

To a stirred solution of anhydrous MeOH (25 mL) was added sodium (300 mg, 13.04 mmol) portionwise. To the clear solution was added SEM-protected 3,5-dinitropyrazole from Step D (1 g, 3.47 mmol) and the mixture was stirred at 60° C. for 2 h. The mixture was allowed to cool to rt and was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0-30% EtOAc/hexane to afford a single regioisomer of SEM-protected 3-methoxy-5-nitropyrazole (SEM=((2-(trimethylsilyl)ethoxy)methyl)) as a clear oil (723 mg, 76%). 1H NMR (300 MHz, CDCl3) δ 6.23 (s, 1H), 5.41 (s, 2H), 4.02 (s, 3H), 3.70-3.65 (m, 2H), 0.96-0.91 (m, 2H), 0.00 (s, 9H).

Workup

  1. temperatureto cool to rt
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was purified by silica gel flash chromatography
  4. washeluting with 0-30% EtOAc/hexane

Sources & evidence

ORD record
ord-ec02fe7840b24b5086c41602bdb6a3f7
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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