Dichloromethane → 8-(3-Pyridinyl)-7-octyn-1-ol

HRID 1249562Notes

Reaction equation

HRID 1249562 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[CH:8].Br[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C(N(CC)CC)C.ClCCl>CCOCC>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]#[C:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:9])[CH:12]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 122863-BromopyridineHCID 701007-Octyn-1-ol

Product 1

HCID 137545048-(3-Pyridinyl)-7-octyn-1-olYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 34.6 g of 7-octyn-1-ol 26.4 mL of 3-bromopyridine, 115 mL of triethylamine and 350 mL of dichloromethane was stirred and flushed with argon. To the mixture was added 3.85 g of bis triphenylphosphine palladium II chloride and 0.365 g of cuprous iodide and then the mixture was refluxed overnight. The cooled reaction mixture was diluted with ether and the solids were filtered, washed well with ether, and then discarded. The filtrates were extracted repeatedly with 1N hydrochloric acid and the combined aqueous layers were made strongly basic with excess sodium hydroxide. The mixture was extracted with dichloromethane, dried over sodium sulfate and evaporated to provide 51 g (91%) of crude 8-(3-pyridinyl)-7-octyn-1-ol. Catalytic hydrogenation in 1000 mL of ethanol using 5 g of 10% palladium on carbon provided, after distillation, 36 g (72%) of 3-pyridineoctanol, bp 145°-152° C. (0.3 mm). Analysis Calculated for C13H21NO: C, 75.32; H, 10.21; N, 6.76. Found: C, 75.13; H, 10.21; N, 6.66.

Workup

  1. customflushed with argon
  2. additionTo the mixture was added 3.85 g of bis triphenylphosphine palladium II chloride and 0.365 g of cuprous iodide
  3. temperaturethe mixture was refluxed overnight
  4. customThe cooled reaction mixture
  5. filtrationthe solids were filtered
  6. washwashed well with ether
  7. extractionThe filtrates were extracted repeatedly with 1N hydrochloric acid
  8. extractionThe mixture was extracted with dichloromethane
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-94a355ccdea9452588e8e2109c2febf1
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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