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

HRID 1605782Notes

Reaction equation

HRID 1605782 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[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:7][CH2:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6456Trityl chlorideHCID 702345-Hexyn-1-ol

Product 1

HCID 203810371,1',1''-{[(Hex-5-yn-1-yl)oxy]methanetriyl}tribenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 9.81 g. (0.10 moles) of 5-hexyn-1-ol, 33.5 g. (0.12 moles) of triphenylmethyl chloride, and 200 ml. of dry pyridine is refluxed for 60 minutes. The cooled mixture is poured into water and extracted with ether. The extract is washed successively with water, ice-cold N hydrochloric acid, water, saturated sodium bicarbonate solution, and saturated sodium chloride solution. The extract is dried with magnesium sulfate. The crude product obtained after evaporation of the solvent is purified by chromatography on Florisil to give an oil, νmax. 3290 (acetylenic hydrogen), 1600, 1072, and 705 cm-1 (triphenylmethoxy group).

Workup

  1. additionA stirred mixture of 9.81 g
  2. extractionextracted with ether
  3. washThe extract is washed successively with water, ice-cold N hydrochloric acid, water, saturated sodium bicarbonate solution, and saturated sodium chloride solution
  4. dry with materialThe extract is dried with magnesium sulfate

Sources & evidence

ORD record
ord-fcc705d56aed4f12958ba1795bd859fe
Source dataset
uspto-grants-1976_04
Patent number
US03950406

Reaction notes

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