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

HRID 1770167Notes

Reaction equation

HRID 1770167 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

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##

Workup

  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)

Sources & evidence

ORD record
ord-f200ceb44f0e42098f2d4ce26f9c3aeb
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

Loading…