Trifluoroacetic acid → 5,7-Bis(1,1-dimethylethyl)-3-phenyl-(3H)-benzofuran-2-one

HRID 1611730

Reaktionsgleichung

Reaktionsgleichung von HRID 1611730
[CH:1](=[C:8]1[C:13](=[O:14])[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)[C:25](O)=[O:26]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]([C:10]1[CH:11]=[C:12]([C:15]([CH3:16])([CH3:18])[CH3:17])[C:13]2[O:14][C:25](=[O:26])[CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]=2[CH:9]=1)([CH3:22])([CH3:21])[CH3:20]

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 54208733HCID 54208733, Verbindung2×

Produkt 1

HCID 64553565,7-Bis(1,1-dimethylethyl)-3-phenyl-(3H)-benzofuran-2-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 589 mg (2.0 mmol) of a mixture of 6-benzylidene-2,4-di-tert-butyl-cyclohexa-2,4-dienone (compound (302), Table 3) and the corresponding dimer (compound (402), Table 4), prepared according to Example 2b, in 7 ml of toluene is degassed using argon and then 58 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium(0) and 23 mg (0.20 mmol) of trifluoroacetic acid are added. The autoclave is flushed with carbon monoxide and sealed, and a carbon monoxide pressure of 5 bar is then applied. The reaction mixture is maintained at 80° C. for 20 hours. After cooling to room temperature, the reaction mixture is poured into water and extracted three times using ethyl acetate. The organic phases are combined, dried over sodium sulfate and concentrated using a vacuum rotary evaporator. Crystallisation of the residue from isopropanol yields 580 mg (90%) of 5,7-di-tert-butyl-3-phenyl-3H-benzofuran-2-one (compound (102), Table 1), m.p. 116-119° C. Analysis, calculated: C 81.95; H 8.13%. Analysis, found: C 81.93; H 8.13%.

Aufarbeitung

  1. customis degassed
  2. customThe autoclave is flushed with carbon monoxide
  3. customsealed
  4. temperatureAfter cooling to room temperature
  5. additionthe reaction mixture is poured into water
  6. extractionextracted three times
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customa vacuum rotary evaporator
  10. customCrystallisation of the residue from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-7fb6dfad001e4eb289da315bb5973d59
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06989446B2

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