Pyridine → 3-Triphenylmethoxy-1-octyne

HRID 1448224Notes

Reaction equation

HRID 1448224 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°, νmax. (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°, νmax

Sources & evidence

ORD record
ord-654f1ab230df4af784c2a77a5d7ba204
Source dataset
uspto-grants-1979_12
Patent number
US04179574

Reaction notes

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