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

HRID 2093335
Notes
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Reaction equation

HRID 2093335 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-67403ac794434d19a67210b49423a45b
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08445483B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes