Trifluoroacetic acid → 5-(4-Chloro-2-methoxybenzyl)-1,3-thiazole

HRID 272747Notes

Reaction equation

HRID 272747 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[S:14][CH:13]=[N:12][CH:11]=2)O)=[C:4]([O:15][CH3:16])[CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:10]2[S:14][CH:13]=[N:12][CH:11]=2)=[C:4]([O:15][CH3:16])[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69219630(4-Chloro-2-methoxyphenyl)(1,3-thiazol-5-yl)methanol

Product 1

HCID 692195725-(4-Chloro-2-methoxybenzyl)-1,3-thiazoleYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 679A (204 mg, 0.8 mmol), trifluoroacetic acid (0.87 mL, 8 mmol), and triethylsilane (1.27 mL, 8 mmol) in methylene chloride was stirred at room temperature for 5 days. The solution was concentrated under vacuum, diluted with methylene chloride, and poured into 2M NaOH. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was then purified by flash column chromatography on silica gel with 1:1 hexanes/methylene chloride to provide 108 mg (57%) of the title compound. MS (ESI) m/e 240 (M+H)+, 1H NMR (DMSO-d6, 300 MHz): □ 8.88 (s, 1H), 7.67 (s, 1H), 7.21 (d, J=7.80 Hz, 1H), 7.07 (d, J=2.03 Hz, 1H), 6.96 (dd, J=7.80, 2.03 Hz, 1H), 4.10 (s, 2H), 3.84 (s, 3H).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. additiondiluted with methylene chloride
  3. additionpoured into 2M NaOH
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was then purified by flash column chromatography on silica gel with 1:1 hexanes/methylene chloride

Sources & evidence

ORD record
ord-b5010b193b024a81943eb88a27c9a20e
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

Loading…