Borane;tetrahydrofuran → HCID 12511634, compound

HRID 656297Notes

Reaction equation

HRID 656297 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=[C:3]1[CH:10]=[O:11].B.O1CCCC1>O1CCCC1>[OH:11][CH2:10][C:3]1[N:2]([CH3:1])[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 123454411-Methyl-4-nitro-1H-pyrrole-2-carbaldehyde

Product 1

HCID 12511634HCID 12511634, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 22-1 (550 mg) was dissolved in anhydrous tetrahydrofuran (30 ml) and cooled to 0° C. To the solution was slowly added dropwise 1M borane-tetrahydrofuran (3.25 ml), followed by refluxing at 80° C. for 3 hours. After the completion of the reaction, the solvent was evaporated under reduced pressure to be removed, and then the residue was purified by column-chromatography (ethyl acetate/hexane=2/1) to yield the compound 22-2 (500 mg, 90%).

Workup

  1. temperatureby refluxing at 80° C. for 3 hours
  2. customAfter the completion of the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. customto be removed
  5. customthe residue was purified by column-chromatography (ethyl acetate/hexane=2/1)

Sources & evidence

ORD record
ord-3a50af38c0b84081822610b02952bb68
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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