Tetrabutylammonium Fluoride → HCID 66707624, compound

HRID 1848342Notes

Reaction equation

HRID 1848342 reaction equation
[Si]([O:18][CH2:19][C:20]1([C:23]2[N:33]=[C:26]3[C:27]([O:31][CH3:32])=[CH:28][CH:29]=[CH:30][N:25]3[N:24]=2)[CH2:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[CH3:32][O:31][C:27]1[C:26]2[N:25]([N:24]=[C:23]([C:20]3([CH2:19][OH:18])[CH2:22][CH2:21]3)[N:33]=2)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66707383HCID 66707383, compound

Product 1

HCID 66707624HCID 66707624, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(1-((tert-butyldiphenylsilyloxy)methyl)cyclopropyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine (4.5 g, 9.84 mmol) in dry THF (40 ml) was added TBAF (38.38 mmol, 1M in THF) at RT and the mixture was stirred further. After 16 h, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic phase was dried over anhyd. Na2SO4 and concentrated under reduced pressure. The residue obtained was purified by column chromatography to afford (1-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropyl)methanol (1.7 g, 79%) as a solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic phase was dried over anhyd
  3. concentrationNa2SO4 and concentrated under reduced pressure
  4. customThe residue obtained
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d4680913477b42a5aa92f9854c81c98b
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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