Pyridine → 3-Triphenylmethoxy-1-octyne

HRID 1659018Notes

Reaction equation

HRID 1659018 reaction equation
[CH:1]#[C:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[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.[K+].[Br-]>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:9][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:2]#[CH:1])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 11692BromotriphenylmethaneHCID 131661-Octyn-3-olHCID 253877Potassium Bromide

Product 1

HCID 126753473-Triphenylmethoxy-1-octyne

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.26 g. (10.0 mmoles) of 1-octyn-3-ol, 4.85 g, (15.0 mmoles) of triphenylmethyl bromide, and 50 ml. of dry pyridine is heated at 95°C. for 60 minutes with occasional swirling. The solution is cooled, treated with water, and extracted with ether. The extract is washed successively with water and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The crude product is purified by chromatography on Florisil and rectystallization from petroleum ether to give white crystals, m.p. 65°-66.5°, μ max. (KBr) 3280 (acetylenic hydrogen), 1605, 1030, and 702 cm-1 (triphenylmethoxy group).

Workup

  1. additionA mixture of 1.26 g
  2. temperatureThe solution is cooled
  3. extractionextracted with ether
  4. washThe extract is washed successively with water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by chromatography on Florisil and rectystallization from petroleum ether
  8. customto give white crystals, m.p. 65°-66.5°, μ max

Sources & evidence

ORD record
ord-bbc95cbf7f754d78a1277a2fbed218bf
Source dataset
uspto-grants-1976_06
Patent number
US03966773

Reaction notes

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