Water → HCID 12806679, compound

HRID 1702150Notes

Reaction equation

HRID 1702150 reaction equation
[CH3:1][C:2]([CH3:23])([CH:4]([OH:22])[CH:5]([N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:3].[H-].[Na+].[CH3:26]I.O>CN(C=O)C>[CH3:3][C:2]([CH3:23])([CH:4]([O:22][CH3:26])[CH:5]([N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12806675HCID 12806675, compound

Product 1

HCID 12806679HCID 12806679, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 15.4 g of 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-8-phenoxy-octan-3-ol in 50 ml of DMF is added dropwise to a suspension of 1.6 g of sodium hydride in 50 ml of DMF. The mixture is then stirred for 2 hours under reflux. When it has cooled to room temperature, 3.7 ml of methyl iodide are added. This mixture is stirred for five hours under reflux, 200 ml of water are then added, the reaction mixture is extracted three times with 100 ml of diethyl ether at a time and the combined extracts are washed three times with 50 ml of water at a time, dried over magnesium sulfate and concentrated under reduced pressure. The residue consists of 2.2 g of a yellowish resin. Infrared spectrum (film): 2,930, 2,862, 1,588, 1,576, 1,486, 1,460 1,264, 1,233, 1,126, 1,080, 1,005, 745, 682 and 670 cm-1.

Workup

  1. temperatureunder reflux
  2. stirringThis mixture is stirred for five hours
  3. temperatureunder reflux
  4. extractionthe reaction mixture is extracted three times with 100 ml of diethyl ether at a time
  5. washthe combined extracts are washed three times with 50 ml of water at a time
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-231971645f5945bd9d4eb0d95d91e47f
Source dataset
uspto-grants-1983_04
Patent number
US04380546

Reaction notes

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