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

HRID 1189161Notes

Reaction equation

HRID 1189161 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]>>[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

3

Reactant 2

HCID 79732-BromopyridineHCID 793464-Pentyn-1-ol

Product 1

HCID 109973535-(Pyridin-2-yl)pent-4-yn-1-olYield 88%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (4.46 g, 28.2 mmol) and pent-4-yn-1-ol (2.50 g, 29.7 mmol). Reaction time: 14 hours. The crude residue was purified by flash chromatography (DCM/MeOH 97:3) to yield 4.00 g (24.8 mmol, 88%) of 5-pyridin-2-yl-pent-4-yn-1-ol as a brown oil.

Workup

  1. customReaction time
  2. custom14 hours
  3. customThe crude residue was purified by flash chromatography (DCM/MeOH 97:3)

Sources & evidence

ORD record
ord-8e0cc491651a412faab8a427c430f1bd
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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