Sodium ethoxide → 1-{2-hydroxy-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]-2-trifluoromethylpentyl}-1H-quinolin-4-one

HRID 2106032Notes

Reaction equation

HRID 2106032 reaction equation
[CH3:1][C:2]([C:12]1[CH:13]=[C:14]([C:18]2([CH3:23])[O:22][CH2:21][CH2:20][O:19]2)[CH:15]=[CH:16][CH:17]=1)([CH3:11])[CH2:3][C:4]1([C:7]([F:10])([F:9])[F:8])[CH2:6][O:5]1.[OH:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][CH:26]=1.[O-]CC.[Na+]>C(O)C>[OH:5][C:4]([C:7]([F:9])([F:8])[F:10])([CH2:3][C:2]([CH3:1])([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2([CH3:23])[O:22][CH2:21][CH2:20][O:19]2)[CH:13]=1)[CH3:11])[CH2:6][N:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25](=[O:24])[CH:26]=[CH:27]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 57810032HCID 57810032, compoundHCID 178516385quinolin-4-ol

Product 1

HCID 578097811-{2-hydroxy-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]-2-trifluoromethylpentyl}-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-{3-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]phenyl}-2-methyl-[1,3]dioxolane (0.514 g, 1.55 mmol), 4-hydroxyquinoline (0.433 g, 2.98 mmol), and sodium ethoxide (21 wt. % solution in ethanol, 0.55 mL, 1.49 mmol) in ethanol (4.2 mL) was heated at 85° C. for 14 hours, cooled to room temperature, 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 extracted with methylene chloride. The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate-hexanes as the eluent. The product-rich fractions were concentrated in vacuo to afford 1-{2-hydroxy-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]-2-trifluoromethylpentyl}-1H-quinolin-4-one. Yield: 0.35 g.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with water
  3. concentrationconcentrated in vacuo
  4. customto remove most of the ethanol
  5. additionThe residue was diluted with half saturated aqueous sodium bicarbonate solution
  6. extractionextracted with methylene chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. concentrationThe product-rich fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-de6df738a4184eb0ab57ba11282ed070
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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