Sodium hydride → HCID 10081681, compound

HRID 2092716Notes

Reaction equation

HRID 2092716 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[N:4]1.Cl[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14]>C1COCC1>[CH3:14][Si:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][O:10][CH2:9][N:3]1[CH:7]=[CH:6][N:5]=[N:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178418936HCID 178418936, compound

Product 1

HCID 10081681HCID 10081681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (289 mg; 60% suspension in paraffin oil) in THF (10 ml) was treated under an argon atmosphere at RT dropwise with a solution of 1,2,3-triazole (500 mg) in THF (10 ml). The mixture was stirred at RT for 1 hour and was then treated at 0° C. dropwise with (2-(chloromethoxy)ethyl)trimethylsilane (1.21 g). Stirring was continued for 2 h. The reaction was quenched with water (10 ml), the layers were separated and the aqueous layer once extracted with AcOEt (15 ml). The combined organic layers were dried over MgSO4, filtered and the solvent was removed in vacuo to give the title compound as a crude product that was used without further purification. Colorless liquid (1.5 g). MS (m/e): 198.204 (M-H+).

Workup

  1. stirringStirring
  2. waitwas continued for 2 h
  3. customThe reaction was quenched with water (10 ml)
  4. customthe layers were separated
  5. extractionthe aqueous layer once extracted with AcOEt (15 ml)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cfb6f1d3e9c747c69316779fc408cf38
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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