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

HRID 1665232Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-39a0e09ae8c940cf901f4fcbbacda151
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039502B2

Reaction notes

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