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

HRID 272747노트

반응식

HRID 272747 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b5010b193b024a81943eb88a27c9a20e
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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