Tetrabutylammonium Fluoride → (e)-1-Fluoro-4-tosyloxy-2-butene

HRID 1698752Notes

Reaction equation

HRID 1698752 reaction equation
[S:1]([O:11][CH2:12]/[CH:13]=[CH:14]/[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-:44]>C1COCC1>[F:44][CH2:15]/[CH:14]=[CH:13]/[CH2:12][O:11][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18320921(e)-1,4-Ditosyloxy-2-butene

Product 1

HCID 18320920(e)-1-Fluoro-4-tosyloxy-2-buteneYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-1,4-ditosyloxy-2-butene (256 mg, 0.64 mmol) in 10 mL of THF was added Bu4NF (0.7 mL, 1M in THF, 0.7 mmol). The mixture was heated to reflux for 30 min. Evaporation and purification of the residue by flash column chromatography with hexane:ether/2:1 afforded the product as a colorless oil (60 mg, 38%). 1 H NMR (CDCl3, 300 MHz) δ 7.80 (d, J=8.4 Hz, 2H), 7.36 (d, J=8.4 Hz, 2H), 5.99-5.75 (m, 2H, 4.84 (ddd, JFCH=46.5 Hz, J=4.8, 1.2 Hz, 2H), 4.59-4.56 (m, 2H), 2.46 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 min
  3. customEvaporation and purification of the residue by flash column chromatography with hexane

Sources & evidence

ORD record
ord-800ec848f55848a9a97516fa3e9a58dd
Source dataset
uspto-grants-2002_02
Patent number
US06344179B1

Reaction notes

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