Dichloromethane → Ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

HRID 879345ノート

反応式

HRID 879345 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.Br[C:24]1[S:25][C:26]2[C:32]([O:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[C:31]([C:41](=[O:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:30]([CH3:48])=[CH:29][C:27]=2[N:28]=1.C(Cl)[Cl:50]>>[Cl:50][C:24]1[S:25][C:26]2[C:32]([O:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[C:31]([C:41](=[O:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:30]([CH3:48])=[CH:29][C:27]=2[N:28]=1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 159087Triacetoxyperiodinane2 回HCID 86699782Ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

生成物 1

HCID 86700145Ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

反応条件

温度
0 °C

実験手順

The above residue was dissolved in CH2Cl2 (33 mL), cooled to 0° C. and Dess-Martin periodinane (2.54 g, 5.99 mmol) was added portion-wise. After stirring for 2 h, more Dess-Martin periodinane (0.25 g, 5.99 mmol) was added. After 1 h, reaction was quenched with Na2S2O3 solution and stirred for 30 minutes. The mixture was diluted with CH2Cl2, washed with water, saturated sodium bicarbonate solution, brine and dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 20% EtOAc/Hex) to give product contaminated with ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate 1H NMR (400 MHz, CDCl3): δ 7.88 (s, 1H), 4.42 (q, J=7.2 Hz, 2H), 2.49 (s, 3H), 1.40 (t, J=7.2 Hz, 3H).

後処理

  1. waitAfter 1 h
  2. customreaction
  3. customwas quenched with Na2S2O3 solution
  4. stirringstirred for 30 minutes
  5. additionThe mixture was diluted with CH2Cl2
  6. washwashed with water, saturated sodium bicarbonate solution, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by CombiFlash (0 to 20% EtOAc/Hex)
  11. customto give product

出典と根拠

ORDレコード
ord-ec671ea85364413588080f6691373f54
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

読み込み中…