Water → HCID 21187493, compound

HRID 1383833Notes

Reaction equation

HRID 1383833 reaction equation
[H-].[Na+].I[CH2:4][CH2:5][CH3:6].[Si:7]([O:14][CH2:15][C:16]1[N:20]=[CH:19][NH:18][N:17]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].O>CN(C=O)C>[Si:7]([O:14][CH2:15][C:16]1[N:17]([CH2:4][CH2:5][CH3:6])[N:18]=[CH:19][N:20]=1)([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:9])[CH3:8].[Si:7]([O:14][CH2:15][C:16]1[N:20]=[CH:19][N:18]([CH2:4][CH2:5][CH3:6])[N:17]=1)([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 336431-IodopropaneHCID 178455184HCID 178455184, compound

Product 2

HCID 21187493HCID 21187493, compoundYield 43%HCID 21187495HCID 21187495, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of sodium hydride (60% dispersion in oil, 1.5 g, 37.5 mmol) and 1-iodopropane (4.4 ml, 45 mmol) in anhydrous DMF (100 ml), cooled under nitrogen to 0° C., was added dropwise over 10 min a solution of 3-(tert-butyldimethylsilanyloxymethyl)-1H-1,2,4-triazole (prepared as described in EP-A-421210) (8.0 g, 37.5 mmol) in anhydrous DMF (25 ml). The mixture was stirred under nitrogen at 0° C. for 25 min, more sodium hydride (60% dispersion in oil, 0.45 g, 11.3 mmol) was added, and the mixture was stirred for another 30 min. Water (300 ml) was then added and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with brine (100 ml), dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 40-50% EtOAc/hexane; and alumina, 15% EtOAc/hexane) to yield 4.10 g (43%) of 5-(tert-butyldimethylsilanyloxymethyl)-1-propyl-1H-1,2,4-triazole and 2.97 g (31%) of 3-(tert-butyldimethylsilanyloxymethyl)-1-propyl-1H-1,2,4-triazole as colourless oils.

Workup

  1. stirringthe mixture was stirred for another 30 min
  2. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  3. washThe combined organic extracts were washed with brine (100 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography (silica gel, 40-50% EtOAc/hexane; and alumina, 15% EtOAc/hexane)

Sources & evidence

ORD record
ord-20de30ae4ffe42ddbc563a85b1fee8c0
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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