Hydrochloric Acid → HCID 86657646, compound

HRID 217458Notes

Reaction equation

HRID 217458 reaction equation
[OH-].[K+].[F:3][C:4]([F:24])([F:23])[C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[CH2:15][CH2:16][C:17]#[C:18][Si](C)(C)C.Cl>CO>[CH2:15]([C:6]1[CH:7]=[CH:8][C:9]([C:11]([F:12])([F:14])[F:13])=[CH:10][C:5]=1[C:4]([F:3])([F:23])[F:24])[CH2:16][C:17]#[CH:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86657647HCID 86657647, compound

Product 1

HCID 86657646HCID 86657646, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of KOH (358 mg) in MeOH (30 mL) was added {4-[2,4-bis(trifluoromethyl)phenyl]but-1-yn-1-yl}(trimethyl)silane (1.8 g), followed by stirring at room temperature for 18 hours. The reaction liquid was neutralized with 1 M hydrochloric acid and extracted with ether. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:EtOAc=100:0) to obtain 1-but-3-yn-1-yl-2,4-bis(trifluoromethyl)benzene (426 mg) as a colorless liquid.

Workup

  1. customThe reaction liquid
  2. extractionextracted with ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:EtOAc=100:0)

Sources & evidence

ORD record
ord-f8a3792b47b44106b6e2e44e65b08011
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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