Water → HCID 10263146, compound

HRID 1654172Notes

Reaction equation

HRID 1654172 reaction equation
[O:1]([CH2:9][C:10]1[N:14]=[CH:13][NH:12][N:11]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[H-].[Na+].O.[CH3:18]N(C)C=O>CI>[O:1]([CH2:9][C:10]1[N:11]([CH3:18])[N:12]=[CH:13][N:14]=1)[Si:2]([C:5]([CH3:8])([CH3:6])[CH3:7])([CH3:4])[CH3:3].[O:1]([CH2:9][C:10]1[N:14]=[CH:13][N:12]([CH3:18])[N:11]=1)[Si:2]([C:5]([CH3:8])([CH3:6])[CH3:7])([CH3:4])[CH3:3].[O:1]([CH2:9][C:10]1[N:14]([CH3:18])[CH:13]=[N:12][N:11]=1)[Si:2]([C:5]([CH3:8])([CH3:6])[CH3:7])([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 178455184HCID 178455184, compound

Product 3

HCID 10263146HCID 10263146, compoundHCID 67757478HCID 67757478, compoundHCID 67757768HCID 67757768, compound

Reagents, catalysts & solvents 1

HCID 6328Methyl iodideSolvent

Procedure

A solution of 3-tert-butyldimethylsiloxymethyl-1H-1,2,4-triazole (8.0 g) in N,N-dimethylformamide (20 ml) was added dropwise at 0° C. to a mixture of 60% sodium hydride in oil (1.5 g), methyl iodide (2.8 ml) and N,N-dimethylformamide (80 ml) for 10 minutes. The mixture was stirred for 10 minutes, to which was added water (300 ml), followed by extraction with ethyl acetate (100 ml×3 times). The organic layer was washed with a saturated aqueous sodium chloride solution, which was then dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The concentrate was subjected to a silica gel chromatography, eluting with ethyl acetate-hexane (1:1), then further with ethyl acetate. The object fractions were respectively concentrated under reduced pressure to afford 5-tert-butyldimethylsiloxymethyl-1-methyl-1H-1,2,4-triazole (4.4 g), 3-tert-butyldimethylsiloxymethyl-1-methyl-1H-1,2,4-triazole (2.4 g), and 3-tert-butyldimethylsiloxymethyl-4-methyl-4H-1,2,4-triazole (0.50 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate (100 ml×3 times)
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution, which
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure
  5. washeluting with ethyl acetate-hexane (1:1)
  6. concentrationThe object fractions were respectively concentrated under reduced pressure

Sources & evidence

ORD record
ord-72cb8adcd36d4abfa70504fcd43e4905
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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