HCID 57831706, compound → HCID 66704789, compound

HRID 425249Notes

Reaction equation

HRID 425249 reaction equation
O[CH:2]([C:30]1[S:31][C:32]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:33][CH:34]=1)[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[CH:15]=[C:14]([CH2:16][CH:17]([C:19]3[S:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:22][CH:23]=3)O)[CH:13]=[CH:12][N:11]=2)[CH:5]=1>C1(C)C=CC=CC=1>[CH2:35]([C:32]1[S:31][C:30]([CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][N:7]=[C:6]([C:10]3[CH:15]=[C:14]([CH:16]=[CH:17][C:19]4[S:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:22][CH:23]=4)[CH:13]=[CH:12][N:11]=3)[CH:5]=2)=[CH:34][CH:33]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

3

Reactant 1

HCID 57831706HCID 57831706, compound

Product 1

HCID 66704789HCID 66704789, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4,4′-bis[2-hydroxy-2-(5-hexyl-2-thienyl)ethyl]-2,2′-b ipyridine (1.5 g) was dissolved in 110 g of toluene containing pyridindium p-toluenesulfonate (0.2 g) and reflux was performed for 4 hours using a Dean-Starc device. The solvent was distilled off under reduced pressure, and a residue was dissolved in methylene chloride and washed with a saturated solution of sodium bicarbonate. An organic layer was washed with anhydrous magnesium sulfate and distilled to obtain 1.2 g of a yellow-colored product.

Workup

  1. temperaturereflux
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutiona residue was dissolved in methylene chloride
  4. washwashed with a saturated solution of sodium bicarbonate
  5. washAn organic layer was washed with anhydrous magnesium sulfate
  6. distillationdistilled

Sources & evidence

ORD record
ord-99f5f5a9469645f382959c0f1813ea43
Source dataset
uspto-grants-2012_01
Patent number
US08106198B2

Reaction notes

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