Ethyl Acetate → 1-Ethynyl-4-(methanesulfonyl)benzene

HRID 1644719Notes

Reaction equation

HRID 1644719 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si](C)(C)C)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1.CCCCCC>[C:11]([C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1)#[CH:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 13741615HCID 13741615, compoundHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrate

Product 1

HCID 220426121-Ethynyl-4-(methanesulfonyl)benzeneYield 72.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of (4-methanesulfonyl-phenylethynyl)-trimethyl-silane (20.7 g , 82.0 mmol) in tetrahydrofuran (450 mL) was added tetrabutylammonium fluoride hydrate (8.80 g, 27.3 mmol). An immediate color change from yellow to red was observed. After 5 minutes, the reaction was complete, and the solvent was removed in vacuo. Water was added, and the resulting mixture was then extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was suspended in dichloromethane, and the insoluble material was filtered off. The filtrate was concentrated to give the crude product. Flash chromatography (RediSep® Flash column, 230-400 mesh, 0-25% ethyl acetate in hexane) afforded 1-ethynyl-4-methanesulfonyl-benzene (10.7 g, 72% yield) as a yellow solid.

Workup

  1. customthe solvent was removed in vacuo
  2. additionWater was added
  3. extractionthe resulting mixture was then extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationthe insoluble material was filtered off
  9. concentrationThe filtrate was concentrated
  10. customto give the crude product

Sources & evidence

ORD record
ord-e2309c38225c489383c3b2f0f339bb05
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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