Estragole → HCID 23502832, Verbindung

HRID 1835361

Reaktionsgleichung

Reaktionsgleichung von HRID 1835361
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].B1(B2C3CCCC2CCC3)C2CCCC1CCC2.C[O-].[K+].[F:33][C:34]([F:65])([F:64])[C:35]1[CH:36]=[C:37]([CH:57]=[C:58]([C:60]([F:63])([F:62])[F:61])[CH:59]=1)[CH2:38][N:39]([CH3:56])[C:40](=[O:55])[C:41]1[C:46]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[CH3:53])=[CH:45][C:44](I)=[N:43][CH:42]=1.[Cl-].C(C1C=CC=C(C(C)C)C=1[N+]1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C=1)(C)C>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC(C)(C)C>[F:62][C:60]([F:61])([F:63])[C:58]1[CH:57]=[C:37]([CH:36]=[C:35]([C:34]([F:65])([F:64])[F:33])[CH:59]=1)[CH2:38][N:39]([CH3:56])[C:40](=[O:55])[C:41]1[C:46]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[CH3:53])=[CH:45][C:44]([CH2:3][CH2:2][CH2:1][C:4]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=2)=[N:43][CH:42]=1

Komponenten

9

Edukt 5

HCID 8815EstragoleHCID 27349131,3-Bis(2,6-diisopropylphenyl)imidazolium chlorideHCID 10231844HCID 10231844, VerbindungHCID 113224419-Borabicyclo[3.3.1]nonane dimerHCID 23664618Potassium methoxide

Produkt 1

HCID 23502832HCID 23502832, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

Deoxygenation of a solution of 89 mg (0.58 mmol) 4-allylanisole in 3 ml tetrahydrofuran by three freeze-thaw cycles was followed by addition of 73 mg (0.29 mmol) 9-borabicyclo[3.3.1]nonane dimer at room temperature under an atmosphere of argon. After 1.5 h 43 mg (0.58 mmol) potassium methoxide were added, and stirring was continued for 20 min. In one portion 250 mg (0.432 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide (Example 4) were added, followed by a suspension of 10 mg (0.043 mmol) palladium(II) acetate and 37 mg (0.086 mmol) 1,3-bis-(2,6-diisopropyl-phenyl)-3H-imidazol-1-ium chloride in 0.5 ml tetrahydrofuran. The reaction mixture was heated at reflux for 2 h. Cooling to room temperature was followed by dilution with tert-butyl methyl ether and washing with two portions of 1 M aqueous sodium hydroxide solution. The combined aqueous layers were extracted with tert-butyl methyl ether. The combined organic extracts were dried with magnesium sulfate and concentrated. Column chromatography afforded 184 mg (71%) of the title compound as a light-yellow amorphous mass.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. washwashing with two portions of 1 M aqueous sodium hydroxide solution
  4. extractionThe combined aqueous layers were extracted with tert-butyl methyl ether
  5. dry with materialThe combined organic extracts were dried with magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6d025d1970354e6d98e805b6da2b7a6f
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770637B2

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