Ethanol → 2-Octyl-5-[4-(5-decyloxypyrimidine-2-yl)phenyl]indan

HRID 1770167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1770167
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:21]([O:31][C:32]1[CH:33]=[N:34][C:35]([C:38]2[CH:43]=[CH:42][C:41](Br)=[CH:40][CH:39]=2)=[N:36][CH:37]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:41]3[CH:40]=[CH:39][C:38]([C:35]4[N:36]=[CH:37][C:32]([O:31][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:33][N:34]=4)=[CH:43][CH:42]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 114747935-Decyloxy-2-(4-bromophenyl)pyrimidineHCID 220990862-Octylindane-5-boronic acid

Produkt 1

HCID 200950392-Octyl-5-[4-(5-decyloxypyrimidine-2-yl)phenyl]indanAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

0.30 g (1.09 mM) of 2-octylindan-5-boronic acid, 0.37 g (0.95 mM) of 5-decyloxy-2-(4-bromophenyl)pyrimidine, 1.8 ml of ethanol, 2.5 ml of benzene, 1.5 ml of 2M-sodium carbonate aqueous solution and 0.05 g of tetrakis (triphenylphosphine) palladium (O) were mixed and heat-refluxed for 4 hours under stirring. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration under reduced pressure and dissolved in toluene, followed by drying with anhydrous sodium sulfate. Then, the sodium sulfate was removed from the mixture and the resultant mixture was evaporated to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized two times from a mixture solvent (toluene/acetone) to obtain 0.42 g of 2-octyl-5-[4-(5-decyloxypyrimidine-2-yl)phenyl]indan (Yield: 82.1%). ##STR279##

Aufarbeitung

  1. temperatureheat-refluxed for 4 hours
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration under reduced pressure
  5. dissolutiondissolved in toluene
  6. dry with materialby drying with anhydrous sodium sulfate
  7. customThen, the sodium sulfate was removed from the mixture
  8. customthe resultant mixture was evaporated
  9. customto obtain a residue
  10. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  11. customrecrystallized two times from a mixture solvent (toluene/acetone)

Quellen und Nachweise

ORD-Eintrag
ord-f200ceb44f0e42098f2d4ce26f9c3aeb
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05385692

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