3-Butyn-1-OL → 4-(3-Quinolinyl)-3-butyn-1-ol

HRID 2082163Notes

Reaction equation

HRID 2082163 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:12]([OH:16])[CH2:13][C:14]#[CH:15]>C(N(CC)CC)C.ClCCl>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([C:15]#[C:14][CH2:13][CH2:12][OH:16])[CH:3]=1

Participants

5

Reactant 2

HCID 135663-Butyn-1-OLHCID 214133-Bromoquinoline

Product 1

HCID 106317924-(3-Quinolinyl)-3-butyn-1-olYield 136.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3-bromoquinoline (13.57 mL, 0.10 mol) and 3-butyn-1 ol (9.0 mL, 0.12 mol) in 40 mL of triethylamine and 75 mL of dichloromethane is degassed by bubbling dry nitrogen through it for 15 minutes, and 0.7 g (0.00I mol) of bis(triphenyl-phosphine)palladium dichloride and 0.013 g of cuprous iodide are added. The flask is flushed with nitrogen and the mixture heated to reflux for 5 hours. The cooled mixture is diluted with dichloromethane and washed with water, dried (sodium sulfate), and concentrated to give 27 g of a gold oil. The oil was triturated with diethyl ether to give 18.2 g of the title compound as a tan solid; mp 95.7°-96.7° C.

Workup

  1. customby bubbling dry nitrogen through it for 15 minutes
  2. addition0.7 g (0.00I mol) of bis(triphenyl-phosphine)palladium dichloride and 0.013 g of cuprous iodide are added
  3. customThe flask is flushed with nitrogen
  4. temperaturethe mixture heated
  5. temperatureto reflux for 5 hours
  6. additionThe cooled mixture is diluted with dichloromethane
  7. washwashed with water
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e2eb6741c3644fbcbd78a48e1d8434f8
Source dataset
uspto-grants-1993_02
Patent number
US05187280

Reaction notes

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