Cyclohexanol → 2,7-Bis-cyclohexyloxy-6-methoxy-quinoxaline

HRID 1066720Notes

Reaction equation

HRID 1066720 reaction equation
[H-].[Na+].[CH:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:11]1[CH:20]=[N:19][C:18]2[C:13](=[CH:14][C:15]([O:23][CH3:24])=[C:16]([O:21][CH3:22])[CH:17]=2)[N:12]=1>CN(C=O)C>[CH:3]1([O:9][C:11]2[CH:20]=[N:19][C:18]3[C:13](=[CH:14][C:15]([O:23][CH:24]4[CH2:7][CH2:8][CH2:3][CH2:4][CH2:5]4)=[C:16]([O:21][CH3:22])[CH:17]=3)[N:12]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 225731372-Chloro-6,7-dimethoxyquinoxaline

Product 1

HCID 225731792,7-Bis-cyclohexyloxy-6-methoxy-quinoxaline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF solution (5 mL) of NaH (0.32 g, 8 mmol) under argon, cyclohexanol (0.7 mL, 6.7 mmol) is added dropwise. The mixture is stirred at room temperature for 25 minutes, then 2-chloro-6,7-dimethoxyquinoxaline is added portionwise. The reaction is stirred for 15 minutes at room temperature, at 90° C. for 2 hours, and at 110° C. for 1 hour. The mixture is cooled, quenched with H2O, and partitioned between EtOAcl H2O. The organic layer is washed with H2O and brine, dried (MgSO4), and chromatographed (10% EtOAc/hexanes) to provide a waxy white solid (m .p. 75-78° C.). Anal. Calcd. for C21H28N2O3: C, 70.76; H, 7.92; N, 7.86; Found: C, 70.81; H, 7.79; N, 7.70.

Workup

  1. stirringThe reaction is stirred for 15 minutes at room temperature, at 90° C. for 2 hours
  2. waitat 110° C. for 1 hour
  3. temperatureThe mixture is cooled
  4. customquenched with H2O
  5. custompartitioned between EtOAcl H2O
  6. washThe organic layer is washed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. customchromatographed (10% EtOAc/hexanes)
  9. customto provide a waxy white solid (m .p. 75-78° C.)

Sources & evidence

ORD record
ord-44fa8c087d124f4680a72b5f9559cbc9
Source dataset
uspto-grants-2001_06
Patent number
US06245760B1

Reaction notes

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