Sodium hydride → HCID 90029660, compound

HRID 1488147Notes

Reaction equation

HRID 1488147 reaction equation
[H-].[Na+].[I:3][C:4]1[NH:8][N:7]=[CH:6][C:5]=1[CH3:9].[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15]Cl>C1COCC1>[I:3][C:4]1[N:8]([CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:18])([CH3:17])[CH3:10])[N:7]=[CH:6][C:5]=1[CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 671846205-Iodo-4-methyl-1H-pyrazole2×

Product 1

HCID 90029660HCID 90029660, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaH (0.48 g, 12.2 mmol, 60%) was added to a solution of 5-iodo-4-methyl-1H-pyrazole (compound 250.1, 2.3 g, 11.1 mmol) in THF (20 mL) at 0° C. The mixture was stirred at 0° C. for 30 minutes, then 2-(trimethylsilyl)ethoxymethyl chloride (2.15 mL, 12.2 mmol) was added. The resulting mixture was stirred at room temperature for 3 hours, and then carefully quenched with a small amount of water and partitioned between EtOAc (200 mL) and water (50 mL). The organic layer was washed with brine (50 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified with by silica gel column chromatography (hexanes:EtOAc, 10:1) to yield the title compound as a light yellow oil (3.15 g, 84%). m/z (ES+) 339 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 3 hours
  2. customcarefully quenched with a small amount of water
  3. custompartitioned between EtOAc (200 mL) and water (50 mL)
  4. washThe organic layer was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with by silica gel column chromatography (hexanes:EtOAc, 10:1)

Sources & evidence

ORD record
ord-5b1d53a78857460e8ae266c00cbd961b
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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