Tetrabutylammonium Fluoride → HCID 19025402, compound

HRID 1030983Notes

Reaction equation

HRID 1030983 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][Si](C)(C)C)=[CH:10][C:9]=2[CH3:20])[C:6](=[S:21])[N:5]([CH3:22])[N:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([N:7]2[C:6](=[S:21])[N:5]([CH3:22])[N:4]=[C:3]2[C:2]([F:24])([F:23])[F:1])=[C:9]([CH3:20])[CH:10]=1)#[CH:15]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19025422HCID 19025422, compound

Product 1

HCID 19025402HCID 19025402, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 4.40 g (0.0119 mole) of 3-trifluoromethyl-4,5-dihydro-1-methyl-4-(2-methyl-4-trimethylsilylethynylphenyl)-1,2,4-triazol-5-(1H)-thione in 75 ml of tetrahydrofuran was added 10.8 g (0.0414 mole) of tetrabutylammonium fluoride. This mixture was stirred for about 20 minutes, and the reaction was partitioned between 75 ml of diethyl ether and 150 ml of an aqueous sodium chloride solution. The organic phase was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure, leaving a residue. This residue was purified by column chromatography on silica gel, eluting with diethyl ether, to yield 2.5 g of 4-(4-ethynyl-2-methylphenyl)-3-trifluoromethyl-4,5-dihydro-1-methyl-1,2,4-triazol-5(1H)-thione as an oil, Compound 111 of Table 1. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customthe reaction was partitioned between 75 ml of diethyl ether and 150 ml of an aqueous sodium chloride solution
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationwas filtered
  4. customThe filtrate was evaporated under reduced pressure
  5. customleaving a residue
  6. customThis residue was purified by column chromatography on silica gel
  7. washeluting with diethyl ether

Sources & evidence

ORD record
ord-31ba1a13bad441e8b6437c5a559ab4a5
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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