Sodium ethoxide → HCID 57810005, compound

HRID 2106023Notes

Reaction equation

HRID 2106023 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[OH:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][CH:21]=1.[O-]CC.[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]([OH:11])([C:13]([F:16])([F:15])[F:14])[CH2:12][N:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:20](=[O:19])[CH:21]=[CH:22]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 57809804HCID 57809804, compoundHCID 178516385quinolin-4-ol

Product 1

HCID 57810005HCID 57810005, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-[2-(3-bromophenyl)-2-methylpropyl]-2-trifluoromethyloxirane, 4-hydroxyquinoline (2 equiv.), and sodium ethoxide (21 wt. % solution in ethanol, 1 equiv.) in ethanol was heated at 85° C. for 14 hours, quenched with water, and concentrated in vacuo to remove most of the ethanol. The residue was diluted with half saturated aqueous sodium bicarbonate solution and methylene chloride. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the residue by flash chromatography using ethyl acetate-hexanes gradient and concentration of the product-rich fractions afforded 1-[4-(3-bromophenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one.

Workup

  1. customquenched with water
  2. concentrationconcentrated in vacuo
  3. customto remove most of the ethanol
  4. additionThe residue was diluted with half saturated aqueous sodium bicarbonate solution and methylene chloride
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-c688a395592144cb8c3ccb55bc982b77
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

Loading…