3-Methylbut-1-yne → HCID 69959296, compound

HRID 369736Notes

Reaction equation

HRID 369736 reaction equation
[CH:1]([C:4]#[CH:5])([CH3:3])[CH3:2].C([Li])CCC.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C:19](=[O:24])[C:20]([F:23])([F:22])[F:21]>C1COCC1>[NH2:11][C:12]1[C:13]([C:19]([OH:24])([C:5]#[C:4][CH:1]([CH3:3])[CH3:2])[C:20]([F:23])([F:21])[F:22])=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 690193-Methylbut-1-yneHCID 120519091-(2-Amino-5-fluorophenyl)-2,2,2-trifluoroethanoneHCID 178418339Butyllithium

Product 1

HCID 69959296HCID 69959296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of 1.89 mL of isopropylacetylene in 35 mL of dry THF was added dropwise over 5 min, 10.0 mL of 1.6 M n-butyllithium. The reaction mixture was stirred at 0° for 30 min after which time 828 mg of 1-(2-amino-5-fluorophenyl)-2,2,2-trifluoroethanone was added. The reaction mixture was stirred at 0° for 1.25 h after which time it was quenched with saturated aqueous ammonium chloride and poured onto water. This mixture was extracted twice with ether and the combined extracts were washed with brine dried and evaporated. The residue was purified by column chromatography on silica gel (elution wth ethyl acetate/hexanes) affording 220 mg of the title compound as a tan solid.

Workup

  1. additionwas added dropwise over 5 min
  2. additionwas added
  3. customwas quenched with saturated aqueous ammonium chloride
  4. additionpoured onto water
  5. extractionThis mixture was extracted twice with ether
  6. washthe combined extracts were washed with brine
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (elution wth ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-eeeadb39e1354d3987e5d0b6d5c259d0
Source dataset
uspto-grants-2000_10
Patent number
US06140320

Reaction notes

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