Triethylamine → 6-(Pyridin-3-YL)hex-5-YN-1-OL

HRID 1583429Notes

Reaction equation

HRID 1583429 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([OH:14])[CH2:9][CH2:10][CH2:11][C:12]#[CH:13].C(N(CC)CC)C>ClCCl>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:13]#[C:12][CH2:11][CH2:10][CH2:9][CH2:8][OH:14])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122863-BromopyridineHCID 702345-Hexyn-1-ol

Product 1

HCID 135575516-(Pyridin-3-YL)hex-5-YN-1-OL

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A dry 250 ml B 3-neck flask was fitted with a gas inlet tube extending nearly to the bottom of the flask and was charged with 9.81 ml of 3-bromopyridine, 11.8 g of 5-hexyn-1-ol, 40 ml of distilled triethylamine and 60 ml of dichloromethane. The mixture was degassed with argon for 15 minutes and 0.70 g of bis(triphenylphosphine)palladium dichloride and 0.13 g of cuprous iodide were added. The flask was evacuated and filled three times with argon and the reaction was heated to reflux for 2 hours. The cooled mixture was diluted with dichloromethane and was washed with water and brine, dried (potassium carbonate) and concentrated to 20 g of a dark red oil which was used directly in the next step. A portion was chromatographed over 70 g of silica gel eluting with 1:1 ethyl acetate-hexane containing 1% triethylamine to yield a colorless oil which was evaporatively distilled, bp 145°-150° C./0.1 mm to give an analytical sample of 6-(3-pyridinyl)-5-hexyn-1-ol.

Workup

  1. customA dry 250 ml B 3-neck flask was fitted with a gas inlet tube
  2. customThe mixture was degassed with argon for 15 minutes
  3. addition0.70 g of bis(triphenylphosphine)palladium dichloride and 0.13 g of cuprous iodide were added
  4. customThe flask was evacuated
  5. additionfilled three times with argon
  6. temperaturethe reaction was heated
  7. temperatureto reflux for 2 hours
  8. additionThe cooled mixture was diluted with dichloromethane
  9. washwas washed with water and brine
  10. dry with materialdried (potassium carbonate)
  11. concentrationconcentrated to 20 g of a dark red oil which
  12. customA portion was chromatographed over 70 g of silica gel eluting with 1:1 ethyl acetate-hexane containing 1% triethylamine
  13. customto yield a colorless oil which
  14. distillationwas evaporatively distilled

Sources & evidence

ORD record
ord-1793a6b3818c4cadba7b2e8d3501bf3c
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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