Tetrahydrofuran → 1-(4-bromo-1H-pyrazol-1-yl)-2-methylbut-3-en-2-ol

HRID 595198Notes

Reaction equation

HRID 595198 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7]C(=O)C)[CH:6]=1.[CH:11]([Mg]Br)=C.[CH2:15]1C[O:18][CH2:17][CH2:16]1>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:17]([CH3:11])([OH:18])[CH:16]=[CH2:15])[CH:6]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 195769081-(4-bromo-1H-pyrazol-1-yl)propan-2-oneHCID 178418507HCID 178418507, compound

Product 1

HCID 1182088221-(4-bromo-1H-pyrazol-1-yl)-2-methylbut-3-en-2-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0° C.) solution of 1-(4-bromo-1H-pyrazol-1-yl)propan-2-one (660 mg, 3.25 mmol) in THF (1 mL) was added vinyl magnesium bromide (1M in THF, 3.9 mL, 3.9 mmol) dropwise over 5 min. The resulting mixture was stirred for 1 h, diluted with 0.5 M HClaq and EtOAc and the layers separated. The organic phase was dried with MgSO4, filtered and concentrated in vacuo, then the crude residue was absorbed on silica gel and purified by column chromatography (0 to 100% EtOAc/Hex) to afford 1-(4-bromo-1H-pyrazol-1-yl)-2-methylbut-3-en-2-ol, MS ESI calcd. for C8H12BrN2O [M+H]+ 231. found 231.

Workup

  1. customthe layers separated
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customthe crude residue was absorbed on silica gel
  6. custompurified by column chromatography (0 to 100% EtOAc/Hex)

Sources & evidence

ORD record
ord-dd5d698d5e2040c79378fda9dc25728b
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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