Pyridine → Trifluoro-methanesulfonic acid 2-(3-benzyloxy-propoxy)-4-chloro-6-formyl-phenyl ester

HRID 2367998ノート

反応式

HRID 2367998 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:14]([OH:22])=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH:16]=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[O:29](S(C(F)(F)F)(=O)=O)[S:30]([C:33]([F:36])([F:35])[F:34])(=O)=[O:31]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:15]([CH:16]=[O:17])[C:14]=1[O:22][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:31])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 866647393-(3-Benzyloxy-propoxy)-5-chloro-2-hydroxy-benzaldehyde

生成物 1

HCID 87109762Trifluoro-methanesulfonic acid 2-(3-benzyloxy-propoxy)-4-chloro-6-formyl-phenyl ester収率 51.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3-(3-benzyloxy-propoxy)-5-chloro-2-hydroxy-benzaldehyde (5.3 g, 16.6 mmol) and pyridine (3.4 mL, 41.5 mmol) in CH2Cl2 (70 mL) at 0° C. was added Tf2O (3.1 mL, 18.3 mmol) drop-wise over 5 minutes period and the reaction mixture was stirred for 3 h at room temperature. The solution was diluted with CH2Cl2 (100 mL), washed with water, brine, dried over Na2SO4, then concentrated under reduced pressure. The product was purified by silica gel column chromatography (2:1 hexanes-EtOAc mobile phase) generating the title compound (3.8 g, 8.5 mmol, 51%) as a light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.18 (s, 1H), 7.48 (d, J=2.3 Hz, 1H), 7.37-7.29 (m, 6H), 4.52 (s, 2H), 4.23 (t, J=6.2 Hz, 2H), 3.69 (t, J=5.8 Hz, 2H), 2.16 (t, J=6.0 Hz, 2H); 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −73.23 (s).

後処理

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by silica gel column chromatography (2:1 hexanes-EtOAc mobile phase)

出典と根拠

ORDレコード
ord-e657c9a9619b426cbce0c666ebdaf904
出典データセット
uspto-grants-2014_04
特許番号
US08703742B2

反応ノート

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