Pyridine → 4-Triphenylmethoxy-1-Octyne

HRID 461269Notes

Reaction equation

HRID 461269 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].[C:10]1([C:16](Br)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1>O>[C:10]1([C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11692BromotriphenylmethaneHCID 1036561-Octyn-4-ol

Product 1

HCID 127861654-Triphenylmethoxy-1-Octyne

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g. (0.08 moles) of 4-hydroxy-1-octyne [L. Crombie and A. G. Jacklin, J. Chem. Soc., 1632 (1957)] and 30.75 g. (0.09 moles) of triphenylmethyl bromide in 85 ml. of dry pyridine is heated on the steam bath for 2 hours. The cooled mixture is treated with water and extracted with ether. The extract is washed successively with ice cold 2% hydrochloric acid, saturated sodium chloride solution, dried with magnesium sulfate, and taken to dryness. Column chromatography of the residue on Florisil affords an oil; λ max 3.01, 4.72 (acetylenic hydrogen), 6.28 9.65 and 14.25 μ (triphenylmethoxy group).

Workup

  1. additionA mixture of 10 g
  2. extractionextracted with ether
  3. washThe extract is washed successively with ice cold 2% hydrochloric acid, saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. customColumn chromatography of the residue on Florisil affords an oil

Sources & evidence

ORD record
ord-5e40d2260646445ab311d47721894684
Source dataset
uspto-grants-1977_12
Patent number
US04061672

Reaction notes

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