Toluene → 5-(2-Octyl-benzo[1,3]dioxol-5-yl)-2-octyloxypyridine

HRID 1779262Notes

Reaction equation

HRID 1779262 reaction equation
[CH2:1]([CH:9]1[O:13][C:12]2[CH:14]=[CH:15][C:16](B(O)O)=[CH:17][C:11]=2[O:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[N:26][CH:27]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].O.C(O)C>[CH2:1]([CH:9]1[O:13][C:12]2[CH:14]=[CH:15][C:16]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[N:26][CH:27]=3)=[CH:17][C:11]=2[O:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 144392315-bromo-2-(octyloxy)PyridineHCID 190503132-Octyl-benzo[1,3]dioxole-5-boronic acid

Product 1

HCID 190502875-(2-Octyl-benzo[1,3]dioxol-5-yl)-2-octyloxypyridine

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5 mmol of 2-octyl-benzo[1,3]dioxole-5-boronic acid and 5 mmol of 5-bromo-2-octyloxypyridine are introduced into a mixture of 30 ml of toluene, 15 ml of ethanol and 15 ml of water. 0.05 mmol of tetrakis(triphenylphosphine)palladium(O) and 12 mmol of sodium carbonate are added, and the mixture is refluxed for 6 hours. The phases are separated, the aqueous phase is extracted with tert-butyl methyl ether, and the combined organic phases are dried by means of Na2SO4. For further purification, the substance is chromatographed on silica gel.

Workup

  1. temperaturethe mixture is refluxed for 6 hours
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with tert-butyl methyl ether
  4. dry with materialthe combined organic phases are dried by means of Na2SO4
  5. customFor further purification
  6. customthe substance is chromatographed on silica gel

Sources & evidence

ORD record
ord-ee4a009f4b65474ba52575dbfaade247
Source dataset
uspto-grants-1997_05
Patent number
US05626791

Reaction notes

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