Tetrabutylammonium Fluoride → HCID 15171473, compound

HRID 981564Notes

Reaction equation

HRID 981564 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][N:20]([CH2:22][CH2:23][N:24]1[C:28](=[O:29])[CH:27]([CH:30](C)[CH2:31][C:32](C)([O:37][SiH3])C(C)(C)C)[S:26][CH:25]1[C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[CH3:21]>O1CCCC1>[CH3:19][N:20]([CH2:22][CH2:23][N:24]1[C:28](=[O:29])[CH:27]([CH2:30][CH2:31][CH2:32][OH:37])[S:26][CH:25]1[C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[CH3:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 137329601HCID 137329601, compound

Product 1

HCID 15171473HCID 15171473, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A lM solution (15 ml) of tetrabutylammonium fluoride in tetrahydrofuran was added dropwise to a solution of 3-dimethylaminoethyl-5-(3-t-butyldimethyl-silyloxypropyl)-2-(3-pyridyl)thiazolidin-4-one (2.6 g, 6.02 mmol) in dry tetrahydrofuran (12 ml) under cooling with ice. Then the mixture was stirred at room temperature for 2 hours to complete the reaction. Saturated aqueous NaHCO (10 ml) was added dropwise to the product mixture, and the resulting aqueous layer was extracted 6 times with ethyl acetate. The extract wad dried over MgSO4, and the solvent was removed under reduced pressure. The residual crude product was purified by medium-pressure liquid chromatography (Si-60® Art. 9385, eluent : hexane : ethanol : aqueous ammonia = 3000 : 400 : 50), giving 3-dimethylaminoethyl-5-(3-hydroxypropyl)-2-(3-pyridyl)thiazolidin-4-one (1.7 g, 88% yield).

Workup

  1. temperatureunder cooling with ice
  2. customthe reaction
  3. extractionthe resulting aqueous layer was extracted 6 times with ethyl acetate
  4. dry with materialThe extract wad dried over MgSO4
  5. customthe solvent was removed under reduced pressure
  6. customThe residual crude product was purified by medium-pressure liquid chromatography (Si-60® Art. 9385, eluent : hexane : ethanol : aqueous ammonia = 3000 : 400 : 50)

Sources & evidence

ORD record
ord-9b3d3e2b412d462ca4bc3f9096d094ce
Source dataset
uspto-grants-1991_02
Patent number
US04992455

Reaction notes

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