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

HRID 272747ノート

反応式

HRID 272747 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b5010b193b024a81943eb88a27c9a20e
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

反応ノート

読み込み中…