Tetrabutylammonium Fluoride Trihydrate → HCID 86642678, compound

HRID 2095390Notes

Reaction equation

HRID 2095390 reaction equation
C([Si](C(C)C)(C(C)C)[N:5]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])=[CH:6]1)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[NH:5]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])=[CH:6]1

Participants

5

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 68185504HCID 68185504, compound

Product 1

HCID 86642678HCID 86642678, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-butyl 3-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]acrylate (10.0 g, 28.7 mmol) in 200 mL of THF was added tetra-n-butylammonium fluoride trihydrate (7.5 g, 23.8 mmol, 0.83 equiv.) at room temperature under N2. The solution was stirred for 30 min at room temperature, diluted with EtOAc (500 mL), and washed with water (2×100 mL). The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column, which was eluted with EtOAc/petroleum ether 1:5 to afford (E)-butyl 3-(1H-pyrrol-3-yl)acrylate (4.0 g, 72%) as a light yellow solid. LC-MS (ESI) m/z 194 (M+H+).

Workup

  1. washwashed with water (2×100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. washwas eluted with EtOAc/petroleum ether 1:5

Sources & evidence

ORD record
ord-401d269b5bc6413b971889a0bd61a452
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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