1-(6-Bromopyridin-2-yl)prop-2-yn-1-one → 2-(6-Bromopyridin-2-yl)but-3-yn-2-ol
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[C:9]#[CH:10])[CH:5]=[CH:4][CH:3]=1.[CH3:12][Mg]Cl>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:11])([C:9]#[CH:10])[CH3:12])[CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
1-(6-Bromopyridin-2-yl)prop-2-yn-1-one (840 mg, 4.00 mmol) was dissolved in THF (20 mL) and cooled to −78° C. Methylmagnesium chloride (3.0 M in THF, 1.60 mL, 4.80 mmol) was added dropwise. The mixture was allowed to warm to room temperature, quenched with saturated NH4Cl, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-50% EtOAc/hexanes) afforded the title compound as a yellow oil.
Workup
- temperatureto warm to room temperature
- customquenched with saturated NH4Cl
- extractionextracted with EtOAc (2×)
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-e66b7b07e9984691aae74ea75eb7f715
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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