Methane → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-ol

HRID 417928Notes

Reaction equation

HRID 417928 reaction equation
[NH:1]1[CH:5]=[C:4]([B:6]2[O:14][C:11]([CH3:13])([CH3:12])[C:8]([CH3:10])([CH3:9])[O:7]2)[CH:3]=[N:2]1.C1(=O)O[CH2:18][CH2:17][O:16]1.[OH-].[Na+].C>CN(C=O)C>[CH3:12][C:11]1([CH3:13])[C:8]([CH3:9])([CH3:10])[O:7][B:6]([C:4]2[CH:3]=[N:2][N:1]([CH2:18][CH2:17][OH:16])[CH:5]=2)[O:14]1

Participants

6

Reactant 4

HCID 297MethaneHCID 7303Ethylene carbonateHCID 14798Sodium HydroxideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 457888552-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-olYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Pyrazoleboronic acid pinacol ester (0.25 g, 1.29 mmol), ethylene carbonate (0.125 g, 1.42 mmol) and sodium hydroxide (5 mg, 0.13 mmol) were dissolved in DMF (1 mL) and the reaction mixture was heated to reflux for 2½ h. It was cooled to r.t. before addition of activated charcoal (25 mg). The resulting suspension was stirred at r.t. for 1 h and then filtered through celite, washed with DMF (6 mL) and concentrated in vacuo to give the title compound (0.26 g, 85%) as a yellow oil. LCMS (ES+) 239.18 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2½ h
  3. filtrationfiltered through celite
  4. washwashed with DMF (6 mL)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a705d7627d9d4d3fb96e0309523815b1
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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