Tetrabutylammonium Fluoride → HCID 59589417, compound

HRID 630289Notes

Reaction equation

HRID 630289 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:14][CH:13]=[N:12][C:11]=1[CH:15]=[CH2:16])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:15]([C:11]1[N:12]=[CH:13][S:14][C:10]=1[CH2:9][OH:8])=[CH2:16]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59589314HCID 59589314, compound

Product 1

HCID 59589417HCID 59589417, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-{[(tert-butyldimethylsilyl)oxy]methyl}-4-ethenyl-1,3-thiazole (763 mg, 3.0 mmol) and a tetrabutylammonium fluoride solution (1M in THF; 4 mL, 4.0 mmol) in anhydrous THF (30 mL) was stirred at room temperature for 1.5 hours. The solvent was evaporated, and the residue was treated with EtOAc (50 mL). The solution was extracted with water (3×50 mL) and brine (1×50 mL), dried over MgSO4, filtered, and evaporated. The residue was dried in vacuo, affording (4-ethenyl-1,3-thiazol-5-yl)methanol (370 mg, 87%). The product was used without further purification.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with EtOAc (50 mL)
  3. extractionThe solution was extracted with water (3×50 mL) and brine (1×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-9527a622b13f4f6eaa6632ebc720b581
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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