Sodium borohydride → HCID 66736400, compound

HRID 1640514Notes

Reaction equation

HRID 1640514 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:13]=[O:14])[C:11]=2[N:12]=1.[BH4-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([N:12]=1)=[C:10]([CH2:13][OH:14])[CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 716074383-Methoxyquinoxaline-5-carbaldehyde

Product 1

HCID 66736400HCID 66736400, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 3-methoxy-quinoxaline-5-carbaldehyde (4.05 g, 21.5 mmol; see WO 2006/032466) in EtOH (150 mL) cooled at 0° C., NaBH4 (814 mg, 21.5 mmol) was added in one portion. The reaction mixture was warmed to rt and stirred for 1 h. The mixture was quenched at 0° C. by addition of 1M HCl until H2 evolvement ceased, then concentrated under reduced pressure. The phases were separated between EA and sat. aq. NaHCO3, the org. layer was dried over MgSO4 and concentrated under reduced pressure. The residue was chromatographed on SiO2 (DCM-MeOH—NH4OH: 1000:50:4) to afford the title alcohol as a dark yellow solid (2.92 g, 71% yield).

Workup

  1. temperatureThe reaction mixture was warmed to rt
  2. customThe mixture was quenched at 0° C. by addition of 1M HCl until H2 evolvement
  3. concentrationconcentrated under reduced pressure
  4. customThe phases were separated between EA and sat. aq. NaHCO3
  5. dry with materiallayer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on SiO2 (DCM-MeOH—NH4OH: 1000:50:4)

Sources & evidence

ORD record
ord-ba87d30395664a4fb2055250c5ce0936
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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