Ethyl 4,4,4-trifluoroacetoacetate → 4-Trifluoromethyl-8-propyl-7-hydroxycoumarin

HRID 2074431

Reaction equation

HRID 2074431 reaction equation
[CH2:1]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11])[CH2:2][CH3:3].[F:12][C:13]([F:23])([F:22])[C:14](=O)[CH2:15][C:16](OCC)=[O:17]>[Cl-].[Zn+2].[Cl-].O>[OH:11][C:5]1[C:4]([CH2:1][CH2:2][CH3:3])=[C:9]2[C:8]([C:14]([C:13]([F:23])([F:22])[F:12])=[CH:15][C:16](=[O:17])[O:10]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 2620601,3-Benzenediol, propyl-

Product 1

HCID 537014304-Trifluoromethyl-8-propyl-7-hydroxycoumarinYield 77%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

2-propylbenzene-1,3-diol (J. Med. Chem., 38, pp 4411-4432, 1995) (3.65 g, 24.0 mmol), zinc chloride (3.60 g, 26.4 mmol), and ethyl 4,4,4-trifluoroacetoacetate (4.86 g, 26.4 mmol) were stirred overnight at 110° C. The reaction solution was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated under vacuum. The obtained residue was purified using silica-gel chromatography (chloroform) and then recrystallized with chloroform, and 5.01 g of the title compound (yield 77%) was obtained as pale-brown crystalline powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe obtained residue was purified
  6. customrecrystallized with chloroform

Sources & evidence

ORD record
ord-f96cc53798e64e878eaa111501b118ce
Source dataset
uspto-grants-2011_04
Patent number
US07919509B2

Linked notes

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