Tetrabutylammonium Fluoride → 1-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-[1,2,3]triazole

HRID 1675554

Reaction equation

HRID 1675554 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH:15]=[C:14]([Si](C)(C)C)[N:13]=[N:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH:15]=[CH:14][N:13]=[N:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 577954251-(1,4-dioxa-spiro[4.5]dec-8-yl)-4-trimethylsilanyl-1H-[1,2,3]triazole

Product 1

HCID 574240951-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-[1,2,3]triazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(1,4-dioxa-spiro[4.5]dec-8-yl)-4-trimethylsilanyl-1H-[1,2,3]-triazole (1.60 g, 5.68) in 41 mL of dry THF is treated by a 1M solution of tetrabutylammonium fluoride in THF (9.0 mL, 9.0 mmol). The resulting mixture is stirred for 48 h at room temperature under nitrogen. It is diluted with EtOAc, washed with saturated aqueous ammonium chloride, water and brine, dried over Na2SO4 and concentrated to give 1-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-[1,2,3]triazole.

Workup

  1. washwashed with saturated aqueous ammonium chloride, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-403c3b9670c242a5b7ab93335899bdd7
Source dataset
uspto-grants-2011_08
Patent number
US08003685B2

Linked notes

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