Trifluoroacetic acid → Methyl 4-(thiazol-2-ylmethyl)benzoate

HRID 410462Notes

Reaction equation

HRID 410462 reaction equation
O[CH:2]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl.C1(C)C=CC=CC=1>[S:14]1[CH:15]=[CH:16][N:17]=[C:13]1[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 12017830Methyl 4-(hydroxy(thiazol-2-yl)methyl)benzoate

Product 1

HCID 67249380Methyl 4-(thiazol-2-ylmethyl)benzoateYield 84%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 1140TolueneSolvent

Procedure

The product of Step 1 (4.00 g, 16.05 mmol) was taken up in DCE (80 ml) with triethylsilane (25.6 ml, 160 mmol), and trifluoroacetic acid (24.72 ml, 321 mmol) was added. The reaction was stirred at reflux overnight. The reaction was diluted with toluene and evaporated to dryness. The residue was taken back up in EtOAc, washed with aqueous saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated. Flash chromatography (0-50% EtOAc/hexanes) afforded methyl 4-(1,3-thiazol-2-ylmethyl)benzoate (3.13 g, 13.42 mmol, 84% yield) as a pale yellow gum that crystallized upon standing. MS ESI: [M+H]+ m/z 234.1.

Workup

  1. additionwas added
  2. temperatureat reflux overnight
  3. customevaporated to dryness
  4. washwashed with aqueous saturated NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-03548a5e592b4fd59af91d505735192b
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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