Methyl iodide → HCID 90030398, compound

HRID 1488190Notes

Reaction equation

HRID 1488190 reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([OH:12])[CH:9]=[N:8]1.[C:15]([O-])([O-])=O.[Cs+].[Cs+].CI>O1CCCC1>[CH3:15][O:12][C:10]1[CH:9]=[N:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:14])([CH3:13])[CH3:1])[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 900300951-[[2-(Trimethylsilyl)ethoxy]methyl]-1H-pyrazol-4-ol2×

Product 1

HCID 90030398HCID 90030398, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-ol (compound 280.2, 2.14 g, 10.0 mmol) in tetrahydrofuran (50 mL) was added Cs2CO3 (6.5 g, 20.0 mmol) in portions. To this was added CH3I (1.25 mL, 20.0 mmol) dropwise. The reaction mixture was stirred for 3 h at room temperature, then concentrated under reduced pressure. The resulting residue was dissolved in 100 mL of EtOAc. The solids were filtered off and the filtrate was concentrated under reduced pressure. This resulted in 2.1 g (92%) of the title compound as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in 100 mL of EtOAc
  3. filtrationThe solids were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d68de0b0c2634a80bbbf76b013f3678b
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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