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

HRID 23343Notes

Reaction equation

HRID 23343 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 partition between EtOAc/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; 1H, 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. custompartition between EtOAc/H2O
  6. washThe organic layer is washed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. customchromatographed (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7bb381c853874411a2799197461a2745
Source dataset
uspto-grants-2005_02
Patent number
US06852712B2

Reaction notes

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