Sodium ethoxide → HCID 10365837, compound

HRID 2106000Notes

Reaction equation

HRID 2106000 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([OH:31])=[CH:23][N:22]=1.[O-]CC.[Na+]>C(O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]([OH:11])([C:13]([F:16])([F:15])[F:14])[CH2:12][N:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:31])[CH:23]=[N:22]2)[CH:7]=1

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxiraneHCID 178516801HCID 178516801, compound

Product 1

HCID 10365837HCID 10365837, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (216 mg) and cinnolin-4-ol (V. G. Chapoulaud et al., Tetrahedron, 2000, 56, pp. 5499-5507) (216 mg) in anhydrous ethanol (1.2 mL) was added sodium ethoxide (21 wt. % solution in ethanol, 276 μL). After heating at 85° C. for 16 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (eluted with 40% ethyl acetate-hexanes) to give the title compound as a pale yellow solid (26 mg), m.p. 122° C.-123° C.

Workup

  1. dry with materialdried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative TLC (eluted with 40% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-638d5b6202a44b7bab00a5ea43941927
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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