Water → HCID 66736400, compound

HRID 1666100Notes

Reaction equation

HRID 1666100 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+].C1COCC1.O>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

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 716074383-Methoxyquinoxaline-5-carbaldehyde

Product 1

HCID 66736400HCID 66736400, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 3-methoxy-quinoxaline-5-carbaldehyde (prepared as described in WO 2006/032466, 5.0 g, 26.57 mmol) in EtOH (200 mL) cooled at 0° C., NaBH4 (1.1 g) was added in one portion. The reaction mixture was warmed to rt and THF (50 mL) was added. A clear solution was obtained. The mixture was further stirred at rt for 30 min. Water (200 mL) was added and the volatiles were removed in vacuo. The residue was filtered off, washed with water. The solid was dried under HV to afford the title alcohol as a brown solid (4.8 g, 95% yield).

Workup

  1. temperatureThe reaction mixture was warmed to rt
  2. customA clear solution was obtained
  3. customthe volatiles were removed in vacuo
  4. filtrationThe residue was filtered off
  5. washwashed with water
  6. customThe solid was dried under HV

Sources & evidence

ORD record
ord-f5763d6eae1442a2940940928047c778
Source dataset
uspto-grants-2011_10
Patent number
US08044044B2

Reaction notes

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