Pyridine → HCID 86733357, compound

HRID 1606673Notes

Reaction equation

HRID 1606673 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].N1C=CC=CC=1.[H][H]>[Pd].O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 21544300HCID 21544300, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86733357HCID 86733357, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 35.9 g. of 1-chloro-7,10,13-nonadecatriyne dissolved in 200 ml. of pyridine and 5.4 g. of 5% palladium on barium sulfate was shaken in an atmosphere of hydrogen in a Parr hydrogenator for 1.25 hrs. (pressure drop 21.5 lb.; 0.1 mole hydrogen = 8.5 lb.), then the reaction mixture was poured into water and extracted with ether. The ether extract was washed several times with water, then with dilute hydrochloric acid, followed by saturated aqueous sodium chloride. The ether solution was then dried over sodium sulfate, and evaporated under reduced pressure leaving a residue comprising 1-chloro-cis,cis,cis-7,10,13-nonadecatriene which was further purified by distillation on a shaking short path distillation apparatus, giving 27 g. of 1-chloro-cis,cis,cis-7,10,13--nonadecatriene collected at a jacket temperature of 180°-190°/0.005 mm.

Workup

  1. additionA mixture of 35.9 g
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed several times with water
  5. dry with materialThe ether solution was then dried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5fdbd5731a0746cb8850633f0937772c
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

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