Sodium hydride → HCID 178486826, compound

HRID 1066726Notes

Reaction equation

HRID 1066726 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([OH:11])[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[H-].[Na+].Cl[C:15]1[CH:24]=[N:23][C:22]2[C:17](=[CH:18][C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[CH:21]=2)[N:16]=1>C1COCC1>[CH3:26][O:25][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:27][CH3:28])[N:16]=[C:15]([O:11][C@@H:8]1[CH2:9][CH2:10][C@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][CH2:7]1)[CH:24]=[N:23]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 225731372-Chloro-6,7-dimethoxyquinoxalineHCID 178476602HCID 178476602, compound

Product 1

HCID 178486826HCID 178486826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of cis 4-acetoxy-cyclohexanol (632 mg, 4 mmole) and NaH (60%, 220 mg, 5.5 mmole) in 15 mL of anhydrous THF is refluxed for 0.5 hour before addition of 2-chloro-6,7-dimethoxyquinoxaline (674 mg, 3 mmole). The resulting mixture is continued to be refluxed for two hours. The residue after filtration and concentration is chromatographed on silica gel (ether) to provide acetic acid cis-4-(6,7-dimethoxyquinoxalin-2-yloxy)-cyclohexyl ester (m.p. 150-152° C.). Anal. Calcd. for C18H22N2O5: C, 62.42; H, 6.40; N, 8.09; Found: C, 62.39; H, 6.55; N, 7.82 and cis-4-(6,7-dimethoxyquinoxalin-2-yloxy)cyclohexanol (m.p. 148-150° C.). Anal. Calcd. for C16H20N2O4: C, 63.14; H, 6.62; N, 9.20; Found: C, 62.80; H, 6.76; N, 8.67.

Workup

  1. temperatureto be refluxed for two hours
  2. filtrationThe residue after filtration and concentration
  3. customis chromatographed on silica gel (ether)

Sources & evidence

ORD record
ord-d5c031629f24435f98be3e8331c1cc63
Source dataset
uspto-grants-2001_06
Patent number
US06245760B1

Reaction notes

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