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

HRID 2074431

반응식

HRID 2074431 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f96cc53798e64e878eaa111501b118ce
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919509B2

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