2-Bromopyridine → 5-(Pyridin-2-yl)pent-4-yn-1-ol

HRID 1651101Notes

Reaction equation

HRID 1651101 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([OH:13])[CH2:9][CH2:10][C:11]#[CH:12].C(N(CC)CC)C>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:12]#[C:11][CH2:10][CH2:9][CH2:8][OH:13]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 8471TriethylamineHCID 793464-Pentyn-1-ol

Product 1

HCID 109973535-(Pyridin-2-yl)pent-4-yn-1-olYield 54.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

As in Example 1, 15.8 g of 2-bromopyridine and 8.4 g of 4-pentyn-1-ol were reacted together in 125 mL of dichloromethane in the presence of 4.2 mL of triethylamine, 2.1 g of bis(triphenylphosphine)palladium dichloride and 0.135 g of cuprous iodide. After 48 hours at reflux, the reaction was worked up in the usual manner. Distillation of the crude product yielded 8.8 g of 5-(2-pyridinyl)-4-pentyn-1-ol (bp 115°-120° C./0.25 mm).

Workup

  1. temperatureAfter 48 hours at reflux
  2. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-1ffb03fc6f8a443cb4d086a122a65a3b
Source dataset
uspto-grants-1990_05
Patent number
US04927826

Reaction notes

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