Methyl iodide → HCID 15334433, compound

HRID 962804Notes

Reaction equation

HRID 962804 reaction equation
[CH2:1]([Li])CCC.[Cl:6][C:7]1([C:10]([OH:20])([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH2:11][C:12]#[CH:13])[CH2:9][CH2:8]1.CI>CCCCCC.O1CCCC1.C(OCC)(=O)C>[Cl:6][C:7]1([C:10]([OH:20])([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH2:11][C:12]#[C:13][CH3:1])[CH2:8][CH2:9]1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 15022048HCID 15022048, compoundHCID 178418339Butyllithium

Product 1

HCID 15334433HCID 15334433, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

26.9 ml (63 mmol) of n-butyllithium in hexane are added at -30° C., with stirring under and a nitrogen atmosphere, to a mixture of 6.76 g (30 mmol) of 4-(1-chlorocyclopropyl)4-hydroxy-5-(1,2,4-triazol-1-yl)-1-pentine and 60 ml of absolute tetrahydrofuran. After the end of the addition, stirring is continued at 0° C. for 15 minutes, and then a solution of 4.68 g (33 mmol) of methyl iodide in 30 ml of absolute tetrahydrofuran is added dropwise. Stirring is then continued for an hour at 20° C. The reaction mixture is worked up by diluting with ethyl acetate and subjecting it several times to extraction by shaking with saturated aqueous ammonium chloride solution. The organic phase is dried over sodium sulphate and filtered and the filtrate is concentrated under reduced pressure. This gives 7.2 g of a product which consists to the extent of67.6% of 5-(1-chlorocyclopropyl)-5-hydroxy-6-(1,2,4triazol-1-yl-2-hexine. For purification, the product is chromatographed on silica gel using ethyl acetate. 4.8 g (67% of theory) of 5-(1-chlorocyclopropyl)-5-hydroxy-6-(1,2,4-triazol-1-yl)-2-hexine are obtained in the form of an oil.

Workup

  1. additionAfter the end of the addition
  2. stirringstirring
  3. stirringStirring
  4. waitis then continued for an hour at 20° C
  5. extractionto extraction
  6. stirringby shaking with saturated aqueous ammonium chloride solution
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated under reduced pressure
  10. customFor purification
  11. customthe product is chromatographed on silica gel

Sources & evidence

ORD record
ord-00674eea14f141b486f6f16daca277ff
Source dataset
uspto-grants-1998_06
Patent number
US05760067

Reaction notes

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