5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde → 1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-prop-2-yn-1-ol

HRID 1624397Notes

Reaction equation

HRID 1624397 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]=[O:15])=[CH:4][CH:3]=1.[C:16]([Mg]Br)#[CH:17]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]([OH:15])[C:16]#[CH:17])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 821337925-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 866524111-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-prop-2-yn-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (0.285 g, 1.07 mmol) was dissolved in THF (8 mL) and the solution was cooled to −78° C. Ethynylmagnesium bromide (0.5M in THF, 2.6 mL, 1.28 mmol) was added dropwise and the reaction was allowed to warm to room temperature. After 1 hour the reaction was quenched with aqueous ammonium chloride the submitted to standard workup to yield the title compound.

Workup

  1. temperatureto warm to room temperature
  2. customAfter 1 hour the reaction was quenched with aqueous ammonium chloride the

Sources & evidence

ORD record
ord-9b8056403789448fb00de916638a74ad
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

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