Pyridine → 3-Triphenylmethoxy-1-octyne

HRID 1580372Notes

Reaction equation

HRID 1580372 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 recrystallization from petroleum ether to give white crystals, m.p. 65°-66.5°, ν 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 recrystallization from petroleum ether
  8. customto give white crystals, m.p. 65°-66.5°, ν max

Sources & evidence

ORD record
ord-808f2981e8d540c19fa6a3bea8aa6956
Source dataset
uspto-grants-1976_01
Patent number
US03932479

Reaction notes

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