Potassium Carbonate → 1,2-Epoxy-8-{4-(5-decylpyrimidine-2-yl) phenyl}decane

HRID 1457500

Reaktionsgleichung

Reaktionsgleichung von HRID 1457500
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[CH2:2]1.C12BC(CCC1)CCC2.[CH2:21]([C:31]1[CH:32]=[N:33][C:34]([C:37]2[CH:42]=[CH:41][C:40](Br)=[CH:39][CH:38]=2)=[N:35][CH:36]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>[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.O.CN(C=O)C.C1COCC1>[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([C:40]2[CH:39]=[CH:38][C:37]([C:34]3[N:33]=[CH:32][C:31]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:36][N:35]=3)=[CH:42][CH:41]=2)[CH2:10][CH3:11])[CH2:2]1

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 543758(7-Octenyl)oxiraneHCID 196949125-Decyl-2-(4-bromophenyl) pyrimidine

Produkt 1

HCID 545064881,2-Epoxy-8-{4-(5-decylpyrimidine-2-yl) phenyl}decaneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-17 °C

Versuchsvorschrift

1.36 g (8.8 mmol) of optically active 1,2-epoxy-9-decene and 6 ml of THF were injected, and they were cooled to -17° C. Then, 9-borabicyclo [3.3.1]nonane (0.5M THF solution) was dripped, and stirring at 0° C. was performed for one hour. Then, stirring at room temperature was performed for one hour, and then 0.26 g (0.073 mmol) of tetrakis (triphenylphosphine) palladium, 3.00 g (8.00 mmol) of 5-decyl-2-(4-bromophenyl) pyrimidine, 10 ml of DMF, and 2.21 g (16.0 mmol) of potassium carbonate were added, and stirring at 60° C. was performed for 5 hours. After reactions had been completed, water was added, and extraction with ethyl acetate was performed. The extracted solution was dried, and then the solvent was removed by filtration. Then, refining was performed with a silica gel column chromatography (developing solvent: toluene/ethyl acetate=50/1) and by recrystallization (toluene/methanol) so that 2.10 g of 1,2-epoxy-8-{4-(5-decylpyrimidine-2-yl) phenyl}decane was obtained (yield 58%).

Aufarbeitung

  1. stirringThen, stirring at room temperature
  2. waitwas performed for one hour
  3. stirringstirring at 60° C.
  4. waitwas performed for 5 hours
  5. extractionextraction with ethyl acetate
  6. customThe extracted solution was dried
  7. customthe solvent was removed by filtration
  8. customThen, refining was performed with a silica gel column chromatography (developing solvent: toluene/ethyl acetate=50/1) and by recrystallization (toluene/methanol) so that 2.10 g of 1,2-epoxy-8-{4-(5-decylpyrimidine-2-yl) phenyl}decane
  9. customwas obtained (yield 58%)

Quellen und Nachweise

ORD-Eintrag
ord-e4aec34e966548ef9de758a830861b5b
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849217

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