Diisopropyl Ether → 2,2-Dimethyl-8-phenoxy-4-(1H-1,2,4-triazol-1-yl)octan-3-one

HRID 1702148Notes

Reaction equation

HRID 1702148 reaction equation
[CH3:1][C:2]([CH3:12])([C:4](=[O:11])[CH2:5][N:6]1[CH:10]=[N:9][CH:8]=[N:7]1)[CH3:3].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OC(C)C)(C)C>CN(C)C=O.O>[CH3:3][C:2]([CH3:12])([C:4](=[O:11])[CH:5]([N:6]1[CH:10]=[N:9][CH:8]=[N:7]1)[CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:1]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 24758Sodium hydrideHCID 70986(4-Bromobutoxy)benzeneHCID 1008773,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone

Product 1

HCID 128066742,2-Dimethyl-8-phenoxy-4-(1H-1,2,4-triazol-1-yl)octan-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 14.3 g of 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butan-3-one (cf. German Laid-Open Application DOS No. 2,638,470) in 20 ml of DMF is added dropwise, under a dry nitrogen atmosphere, to a stirred suspension of 2.3 g of sodium hydride in 20 ml of dimethylformamide (DMF), the reaction temperature being kept at 20°-30° C. by cooling; the mixture is subsequently stirred for 20 hours at room temperature. A solution of 19.5 g of 1-bromo-4-phenoxybutane in 20 ml of DMF is then added dropwise at 5°-10° C., with continued stirring, and whilst cooling with ice. After completion of the addition, stirring is continued for 10 hours at 5°-10° C., after which 200 ml of water are added and the mixture is extracted twice with 100 ml of methylene chloride at a time. The combined organic phases are extracted by shaking with water and dried over magnesium sulfate; removal of the solvent under reduced pressure gives an oil from which, on trituration with 20 ml of diisopropyl ether, 17 g of colorless crystals precipitate; melting point 59°-62° C.

Workup

  1. custombeing kept at 20°-30° C.
  2. temperatureby cooling
  3. temperaturewhilst cooling with ice
  4. additionAfter completion of the addition
  5. stirringstirring
  6. waitis continued for 10 hours at 5°-10° C.
  7. extractionthe mixture is extracted twice with 100 ml of methylene chloride at a time
  8. extractionThe combined organic phases are extracted
  9. stirringby shaking with water
  10. dry with materialdried over magnesium sulfate
  11. customremoval of the solvent under reduced pressure
  12. customgives an oil from which

Sources & evidence

ORD record
ord-ded88035ca2a4304af66e1a5907cff70
Source dataset
uspto-grants-1983_04
Patent number
US04380546

Reaction notes

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