Pyridine → 1,1',1''-{[(Hex-5-yn-3-yl)oxy]methanetriyl}tribenzene

HRID 1448357Notes

Reaction equation

HRID 1448357 reaction equation
[OH:1][CH:2]([CH2:6][CH3:7])[CH2:3][C:4]#[CH:5].[C:8]1([C:14](Cl)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CC=CC=1>O>[C:8]1([C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:1][CH:2]([CH2:6][CH3:7])[CH2:3][C:4]#[CH:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6456Trityl chlorideHCID 892235-Hexyn-3-ol

Product 1

HCID 205651061,1',1''-{[(Hex-5-yn-3-yl)oxy]methanetriyl}tribenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 9.81 g. (0.10 moles) of 4-hydroxy-1-hexyne and 33.5 g. (0.12 moles) of triphenylmethyl chloride in 100 ml. of dry pyridine is heated at reflux for 2 hours. The cooled mixture is treated with water and extracted with a hexane-ether mixture. The extract is washed successively with water and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Column chromatography of the residue on Florisil gives an oil, λ max. 3290 (acetylenic hydrogen), 1600, 1030 and 705 cm-1 (triphenylmethoxy group).

Workup

  1. temperatureat reflux for 2 hours
  2. extractionextracted with a hexane-ether mixture
  3. washThe extract is washed successively with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customColumn chromatography of the residue on Florisil gives an oil, λ max

Sources & evidence

ORD record
ord-7fb14b12c5484dddb9baef47a7a012cd
Source dataset
uspto-grants-1979_12
Patent number
US04179451

Reaction notes

Loading…