Tetrabutylammonium Fluoride → HCID 15053160, compound

HRID 1088819Notes

Reaction equation

HRID 1088819 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]([CH2:22][C:23]#[C:24][Si](C)(C)C)[CH2:19][CH2:18][CH2:17]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]([CH2:22][C:23]#[CH:24])[CH2:19][CH2:18][CH2:17]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15053164HCID 15053164, compound

Product 1

HCID 15053160HCID 15053160, compoundYield 106.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-(2-benzimidazolyl)thiomethyl-1-(3-trimethylsilyl-2-propinyl)-1,2,3,4-tetrahydroquinoline (400 mg) in tetrahydrofuran (20 ml) was added 1M solution of tetra-n-butylammonium fluoride with stirring under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. After distilling off the solvent, the resulting residue was extracted with dichloromethane. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (5.5:1)], and recrystallized from dichloromethane-diethyl ether to give 8-(2-benzimidazolyl)thiomethyl-1-propargyl-1,2,3,4-tetrahydroquinoline (0.35 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes at the same temperature
  3. distillationAfter distilling off the solvent
  4. extractionthe resulting residue was extracted with dichloromethane
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (5.5:1)]
  9. customrecrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-c7fe660fda8b4906909966cbce6c2bf9
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

Loading…