Benzene → 5-(5-Decylpyrimidine-2-yl)-2-octylcoumaran

HRID 3065Notes

Reaction equation

HRID 3065 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)[O:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[C:22]1[N:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:24][N:23]=1.C1C=CC=CC=1.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.O>[CH2:28]([C:25]1[CH:24]=[N:23][C:22]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[O:10][CH:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:17]3)=[N:27][CH:26]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 189343232-Octylcoumaran-5-boronic acidHCID 220990832-Chloro-5-decylpyrimidine

Product 1

HCID 189343145-(5-Decylpyrimidine-2-yl)-2-octylcoumaranYield 23.9%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, 0.30 g (1.09 mM) of 2-octylcoumaran-5-boronic acid, 0.26 g (1.02 mM) of 2-chloro-5-decylpyrimidine and 1.5 ml of benzene were placed in a 20 ml-round-bottomed flask. Under stirring, 0.06 g of tetrakis(triphenylphosphine) palladium (0) and 1.5 ml of a 2M-sodium carbonate aqueous solution were added to the mixture, followed by refluxing for 5.5 hours. After the reaction, the reaction mixture was poured into water and subjected to extraction with ethyl acetate. The organic layer was washed with water, dried with mirabilite and concentrated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography and recrystallized from a mixture solvent of toluene and methanol to obtain 0.11 g of 5-(5-decylpyrimidine-2-yl)-2-octylcoumaran (Ex. Comp. No-I-17) (Yield: 22.5%). The product showed the following phase transition temperatures (°C.). ##STR96##

Workup

  1. temperatureby refluxing for 5.5 hours
  2. customAfter the reaction
  3. extractionsubjected to extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried with mirabilite
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a residue
  8. customThe residue was purified by silica gel column chromatography
  9. customrecrystallized from a mixture solvent of toluene and methanol

Sources & evidence

ORD record
ord-03e5f7ccfb154de09af0ec7af5397bc8
Source dataset
uspto-grants-1998_03
Patent number
US05733476

Reaction notes

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