Ethylene carbonate → 2-(4-Bromo-1H-pyrazol-1-yl)ethanol

HRID 1627582Notes

Reaction equation

HRID 1627582 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].[O:9]1[CH2:13][CH2:12]OC1=O.CCOC(C)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:12][CH2:13][OH:9])[CH:6]=1

Participants

6

Reactant 4

HCID 7303Ethylene carbonateHCID 8857Ethyl AcetateHCID 163754-BromopyrazoleHCID 24758Sodium hydride

Product 1

HCID 166406422-(4-Bromo-1H-pyrazol-1-yl)ethanolYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromo-1H-pyrazole in DMF was added sodium hydride at room temperature. The mixture was stirred for 30 minutes, [1,3]dioxolan-2-one was added, the mixture was stirred and slowly warmed to room temperature. The reaction was monitored by TLC. After the reaction was done, EtOAc was added, washed with saturated NaHCO3, water and brine, dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel, eluants EtOAc and DCM 10%, to give 2-(4-Bromo-pyrazol-1-yl)-ethanol 0.22 g, yield 34%. 1H NMR (400 MHz, chloroform-D) δ ppm 7.49 (s, 1H) 7.46 (s, 1H) 4.18-4.23 (m, 2H) 3.93-3.98 (m, 2H) 3.09 (s, 1H).

Workup

  1. stirringthe mixture was stirred
  2. washwashed with saturated NaHCO3, water and brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel, eluants EtOAc and DCM 10%

Sources & evidence

ORD record
ord-5ffa1fc060144b7cb00d8ca3d49ccd56
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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