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Ethyl trifluoroacetate → 1,1,1-Trifluoro-4-hydroxy-4-phenanthren-2-yl-but-3-en-2-one

HRID 659306
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HRID 659306 반응식
[H-].[Na+].[F:3][C:4]([F:11])([F:10])[C:5]([O:7]CC)=O.[C:12]([C:15]1[CH:28]=[CH:27][C:26]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]=2[CH:16]=1)(=[O:14])[CH3:13]>O1CCCC1>[F:11][C:4]([F:3])([F:10])[C:5](=[O:7])[CH:13]=[C:12]([OH:14])[C:15]1[CH:28]=[CH:27][C:26]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]=2[CH:16]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydrideHCID 80060Methyl 2-phenanthryl ketone

생성물 1

HCID 766150871,1,1-Trifluoro-4-hydroxy-4-phenanthren-2-yl-but-3-en-2-one수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
25 °C

실험 절차

To a suspension of sodium hydride (NaH; 0.13 g, 5.4 mmol) in 5 mL of anhydrous tetrahydrofuran (THF) was added ethyl trifluoracetate (CF3COOEt; 0.64 g, 4.5 mmol) under argon. After stirring at 25° C. for 10 minutes, 2-acetylphenanthrene (1 g, 4.5 mmol) in 5 mL of THF was added dropwise to the solution. The mixture became clear and orange-hued within 30 minutes, and after stirring for an additional 2 hours, was concentrated under vacuum. The residue was suspended in water, and extracted with ethyl acetate (15 mL) twice. The organic phase was separated, dried over sodium sulfate, and concentrated to dryness under vacuum to give the product (yellow solid; 1.29 g, 90% yield). The product was used directly without further purification.

후처리

  1. waitThe mixture became clear and orange-hued within 30 minutes
  2. stirringafter stirring for an additional 2 hours
  3. concentrationwas concentrated under vacuum
  4. extractionextracted with ethyl acetate (15 mL) twice
  5. customThe organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness under vacuum
  8. customto give the product (yellow solid; 1.29 g, 90% yield)
  9. customThe product was used directly without further purification

출처 및 근거

ORD 기록
ord-0ebb02ab840748d29c685f0509063c5d
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08080574B2

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