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

HRID 1925126Notes

Reaction equation

HRID 1925126 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[O:15]1[CH2:19][CH2:18]OC1=O.[OH-].[Na+].C>CN(C=O)C>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:18][CH2:19][OH:15])[CH:10]=2)[O:3]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 97.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanol was synthesized according to the procedure in PCT Publication No. WO 2008/44022, which is incorporated herein in its entirety. Specifically, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5.0 g, 25.8 mmol), 1,3-dioxolan-2-one (2.5 g, 28.3 mmol), and sodium hydroxide (pellets, 1.0 g, 25.8 mmol) were dissolved in DMF (206 mL). The reaction mixture was heated to reflux for 2 hours. Activated charcoal was added after reaction was cooled to ambient temperature and the reaction was stirred for 1 hr and then filtered through Celite. The filter cake was then rinsed with DMF (120 mL), and the filtrate was concentrated to provide 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanol as a yellow oil (6 g). The resulting material was used without further purification. ESI-MS:m/z 239.3 (M+H)+.

Workup

  1. custom2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanol was synthesized
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 2 hours
  4. customafter reaction
  5. filtrationfiltered through Celite
  6. washThe filter cake was then rinsed with DMF (120 mL)
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-df6b92a5927f4cd98b76ecec462bf4e1
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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