Sodium hydride → 1-(benzyloxymethyl)-1H-tetrazole

HRID 2104952Notes

Reaction equation

HRID 2104952 reaction equation
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.[H-].[Na+].[CH2:8](Cl)[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C=O)C.CCOC(C)=O>[CH2:10]([O:9][CH2:8][N:1]1[CH:5]=[N:4][N:3]=[N:2]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 178418441HCID 178418441, compound

Product 1

HCID 106315241-(benzyloxymethyl)-1H-tetrazoleYield 35.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of tetrazole (500 mg, 7.13 mmol) in 14 mL DMF at 0° C. was added NaH (60%, 286 mg, 7.13 mmol). The mixture was stirred at 0° C. for 20 min, then was treated with BOM-Cl (80%, 1.35 mL, 7.84 mmol). The mixture was stirred at rt for 2 h, then was diluted with EtOAc. The organic phase was washed with H2O (3×) and brine, dried (Na2SO4), filtered through 1″ SiO2 and concentrated. The crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient) to afford 483 mg of Intermediate 12.1 as a colorless oil.

Workup

  1. stirringThe mixture was stirred at rt for 2 h
  2. washThe organic phase was washed with H2O (3×) and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered through 1″ SiO2
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-9a08e09334bd425f9896901f9cf21960
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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