Sodium borohydride → HCID 59410519, compound

HRID 1944983Notes

Reaction equation

HRID 1944983 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=[O:17].[BH4-].[Na+]>C(O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]2[O:17][CH2:16][C:12]3[N:11]([CH:15]=[CH:14][CH:13]=3)[C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59410531HCID 59410531, compound

Product 1

HCID 59410519HCID 59410519, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(2-fluoro-5-nitrophenyl)-1H-pyrrole-2-carbaldehyde (3.95 g, 16.9 mmol) was suspended in ethanol (100 mL) in a 250 mL round bottomed flask and treated with sodium borohydride (767 mg, 20.3 mmol, 1.2 equiv.). The resulting mixture was stirred at 60° C. for 5 hours. The reaction mixture was cooled to ambient temperature, transferred to a separatory funnel and partitioned (CH2Cl2//H2O). The organic phase was washed with H2O (3×50 mL), brine (3×50 mL), dried over Na2SO4 and evaporated in vacuo to give a light yellow residue. The residue was purified by flash chromatography (hexanes→1:9 EtOAc/hexanes) to afford the title compound as a light yellow solid (2.5 g, 68%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customtransferred to a separatory funnel
  3. custompartitioned (CH2Cl2//H2O)
  4. washThe organic phase was washed with H2O (3×50 mL), brine (3×50 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customto give a light yellow residue
  8. customThe residue was purified by flash chromatography (hexanes→1:9 EtOAc/hexanes)

Sources & evidence

ORD record
ord-a1aa4b3e8d9c4d1abe012620e365dbb2
Source dataset
uspto-grants-2013_03
Patent number
US08394951B2

Reaction notes

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