Methanol → HCID 69049446, compound

HRID 1455713Notes

Reaction equation

HRID 1455713 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1)[CH2:14][CH2:13][C:12]2=[O:28])C.[OH-].[K+].CO>O>[O:28]=[C:12]1[C:11]2[C:15](=[CH:16][C:17]([C:18]3[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=3)=[C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:29])=[O:3])[CH:10]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 69051916HCID 69051916, compound

Product 1

HCID 69049446HCID 69049446, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.2 g (3 mmol) of ethyl4-[3-oxo-6-(4-trifluoromethylphenyl)indan-5-yloxy]butyrate are mixed with 250 mg (45 mmol) of potassium hydroxide, 40 ml of methanol and 10 ml of water. The mixture is heated at reflux for 2 hours and the methanol is then evaporated off. The solution obtained is washed with ether; the aqueous phase is acidified and extracted with dichloromethane. The organic phase is dried (Na2SO4) and the solvents are evaporated off: yellow solid (0.95 g). Purification of the compound by flash chromatography (98/2 dichloromethane/methanol) [lacuna] (0.56 g; 50%).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. customthe methanol is then evaporated off
  4. customThe solution obtained
  5. washis washed with ether
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic phase is dried (Na2SO4)
  8. customthe solvents are evaporated off
  9. customPurification of the compound by flash chromatography (98/2 dichloromethane/methanol) [lacuna] (0.56 g; 50%)

Sources & evidence

ORD record
ord-724a9af7b98c40de96baf3f9b75ed0bc
Source dataset
uspto-grants-2009_01
Patent number
US07482484B2

Reaction notes

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