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

HRID 1770167ノート

反応式

HRID 1770167 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 200950392-Octyl-5-[4-(5-decyloxypyrimidine-2-yl)phenyl]indan収率 82.1%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 241Benzene溶媒

実験手順

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##

後処理

  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)

出典と根拠

ORDレコード
ord-f200ceb44f0e42098f2d4ce26f9c3aeb
出典データセット
uspto-grants-1995_01
特許番号
US05385692

反応ノート

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