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

HRID 1457500

반응식

HRID 1457500 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-17 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-e4aec34e966548ef9de758a830861b5b
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849217

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