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

HRID 2419942Notes

Reaction equation

HRID 2419942 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.C#C.[H][H]>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

6

Reactant 4

HCID 1049PyridineHCID 6456Trityl chlorideHCID 892235-Hexyn-3-olHCID 178461831HCID 178461831, compound

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 successsively with water and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Column chromatography of the residue on Florisil gives an oil, λ mas. 3290 (acetylene 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 successsively 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 mas

Sources & evidence

ORD record
ord-2733a1b946d9494c875f66e1ed906534
Source dataset
uspto-grants-1978_08
Patent number
US04107441

Reaction notes

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