Sodium hydride → 1-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-6(2-fluorophenoxy)-hexan-1-one

HRID 620657Notes

Reaction equation

HRID 620657 reaction equation
[CH3:1][C:2]1([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30]>CN(C)C=O>[CH3:1][C:2]1([C:8](=[O:15])[CH:9]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[CH2:7][O:6][CH2:5][O:4][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 71722941-(4-Bromobutoxy)-2-fluorobenzeneHCID 128556521-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one

Product 1

HCID 137154561-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-6(2-fluorophenoxy)-hexan-1-oneYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 42.2 g (0.2 mole) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one in 150 ml of absolute dimethylformamide is added dropwise, at from 20° to 25° C., to a stirred suspension of 5.3 g (0.22 mole) of sodium hydride in 50 ml of absolute dimethylformamide, the suspension being kept under nitrogen. Stirring is continued for 3 hours, after which a solution of 49.4 g (0.2 mole) of 1-bromo-4-(2-fluorophenoxy)-butane in 50 ml of absolute dimethylformamide is added dropwise at 60° C. and the reaction mixture is then refluxed for a further 5 hours. About 100 ml of ice water are then carefully added dropwise at room temperature, and the mixture is extracted with three times 300 ml of methylene chloride. The organic phase is then washed several times with water, dried over Na2SO4 and evaporated down. Distillation (bp.=248° C./0.005) gives 56 g (74%) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-6(2-fluorophenoxy)-hexan-1-one as a yellowish resin.

Workup

  1. temperaturethe reaction mixture is then refluxed for a further 5 hours
  2. extractionthe mixture is extracted with three times 300 ml of methylene chloride
  3. washThe organic phase is then washed several times with water
  4. dry with materialdried over Na2SO4
  5. customevaporated down
  6. distillationDistillation (bp.=248° C./0.005)

Sources & evidence

ORD record
ord-ace80921aee84e0b98a65cdd87dfed91
Source dataset
uspto-grants-1989_04
Patent number
US04822400

Reaction notes

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