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

HRID 2074431

反応式

HRID 2074431 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 537014304-Trifluoromethyl-8-propyl-7-hydroxycoumarin収率 77%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f96cc53798e64e878eaa111501b118ce
出典データセット
uspto-grants-2011_04
特許番号
US07919509B2

関連ノート

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