Tetrabutylammonium Fluoride → HCID 15632071, compound

HRID 1906200Notes

Reaction equation

HRID 1906200 reaction equation
[O:1]([C:9]1[CH:10]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:19])[N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]2)[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:1][C:9]1[CH:10]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:19])[N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 56618060HCID 56618060, compound

Product 1

HCID 15632071HCID 15632071, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-t-butyldimethylsiloxy-3-ethoxycarbonyl-4H-quinolizin-4-one (3.32 g) in tetrahydrofuran (100 ml) was added a solution of tetra-n-butylammonium fluoride (1M, 11.47 ml) at 0° C. The mixture was stirred for one hour and the solvent was distilled off. The residue was dissolved in ethyl acetate, washed with water and saturated sodium chloride solution. After drying over magnesium sulfate, the solvent was filtered and evaporated. The residue was chromatographed on silica gel eluting with chloroform to give 1-hydroxy-3-ethoxycarbonyl-4H-quinolizin-4-one (1.13 g).

Workup

  1. distillationthe solvent was distilled off
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialAfter drying over magnesium sulfate
  5. filtrationthe solvent was filtered
  6. customevaporated
  7. customThe residue was chromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-c8273829d55a420885a6531a5e1a49b7
Source dataset
uspto-grants-1987_03
Patent number
US04650804

Reaction notes

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