6-Bromopyridine-2-carbaldehyde → 1-(6-Bromopyridin-2-yl)prop-2-yn-1-ol

HRID 386065Notes

Reaction equation

HRID 386065 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:10]([Mg]Br)#[CH:11]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:9])[C:10]#[CH:11])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 595262091-(6-Bromopyridin-2-yl)prop-2-yn-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

6-Bromo-2-pyridine carboxaldehyde (3.00 g, 16.13 mmol) was dissolved in THF (50 mL) and cooled to −78° C. Ethynylmagnesium bromide (0.5 M in THF, 45.2 mL, 22.58 mmol) was added, and the reaction was allowed to warm to room temperature over 2 h. It was then quenched with saturated NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (50% EtOAc/hexanes) afforded the title compound as a yellow solid.

Workup

  1. temperatureto warm to room temperature over 2 h
  2. customIt was then quenched with saturated NH4Cl
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ed8026807e6f4f438d36c0fadd9c5111
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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