Water → HCID 21707090, compound

HRID 1384186Notes

Reaction equation

HRID 1384186 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.[CH3:9][Si:10]([CH2:13][CH2:14][O:15][CH2:16]Cl)([CH3:12])[CH3:11].O>C1COCC1>[I:3][C:4]1[CH:5]=[N:6][N:7]([CH2:16][O:15][CH2:14][CH2:13][Si:10]([CH3:12])([CH3:11])[CH3:9])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 770224-IodopyrazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 21707090HCID 21707090, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of NaH (1.94 g, 48.5 mmol) in THF (40 mL) at 0° C. was treated with a solution of 4-iodopyrazole (8.97 g, 46.2 mmol) in THF (20 mL), stirred for 1 h, treated with SEM chloride (9.00 mL, 50.8 mmol), stirred at room temperature for 1 h, poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with 10% ethyl acetate/hexanes to provide 14.4 g of the title compound.

Workup

  1. stirringstirred at room temperature for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1771e4ae94464c48aaaa59d31bb88a1b
Source dataset
uspto-grants-2001_07
Patent number
US06258822B1

Reaction notes

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