2-Bromopyridine → 4-(Pyridin-2-yl)but-3-yn-1-ol

HRID 334527Notes

Reaction equation

HRID 334527 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([OH:12])[CH2:9][C:10]#[CH:11]>>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[C:10][CH2:9][CH2:8][OH:12]

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 135663-Butyn-1-OL

Product 1

HCID 110080634-(Pyridin-2-yl)but-3-yn-1-olYield 64%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (10.3 g, 65.1 mmol) and but-3-yn-1-ol (5.08 mL, 67.1 mmol). Reaction time: 14 hours. The crude residue was purified by flash chromatography (DCM/AcOEt 3:7 to 1:9) to yield 6.10 g (41.4 mmol, 64%) of 4-(pyridin-2-yl)but-3-yn-1-ol as a brown oil.

Workup

  1. customReaction time
  2. custom14 hours
  3. customThe crude residue was purified by flash chromatography (DCM/AcOEt 3:7 to 1:9)

Sources & evidence

ORD record
ord-8a8f49ad6cb6445187aa4e241a79c9b7
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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