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

HRID 2047072Notes

Reaction equation

HRID 2047072 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[CH:11]=[C:10]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)[CH:9]=[N:8]1)(=O)C.C1COCC1.[Li+].[OH-].Cl>O>[CH3:19][C:14]1([CH3:20])[C:15]([CH3:17])([CH3:18])[O:16][B:12]([C:10]2[CH:9]=[N:8][N:7]([CH2:6][CH2:5][OH:4])[CH:11]=2)[O:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 497584812-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 mL roundbottom flask was charged 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl acetate (2.11 mmol, 591 mg), a solution of 2:1 THF:H2O (15 mL), and 1N LiOH(aq) (4.82 mmol, 4.82 mL). The resulting solution was stirred at room temperature for 48 hours. At 48 hours, the reaction was quenched with 1N HCl(aq) (4.82 mmol, 4.82 mL) and the solvent removed in vacuo. The product was taken forward without further purification.

Workup

  1. waitAt 48 hours
  2. customthe solvent removed in vacuo
  3. customThe product was taken forward without further purification

Sources & evidence

ORD record
ord-b217274f47f34d1e8f1ea2aa44f412b2
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

Loading…