5-{[3-(Tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-hydroxy-methyl}-2-chloro-benzenesulfonamide → 5-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-benzoyl]-2-chloro-benzenesulfonamide

HRID 873638ノート

反応式

HRID 873638 の反応式
[C:1]([Si:5]([CH3:29])([CH3:28])[O:6][C:7]1[CH:8]=[C:9]([CH:15]([OH:27])[C:16]2[CH:17]=[CH:18][C:19]([Cl:26])=[C:20]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:21]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]([Si:5]([CH3:29])([CH3:28])[O:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:15]([C:16]1[CH:17]=[CH:18][C:19]([Cl:26])=[C:20]([S:22]([NH2:25])(=[O:23])=[O:24])[CH:21]=1)=[O:27])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 581074595-{[3-(Tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-hydroxy-methyl}-2-chloro-benzenesulfonamideHCID 131709961Jones' reagent

生成物 1

HCID 581075125-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-benzoyl]-2-chloro-benzenesulfonamide収率 50%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 5-{[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-hydroxy-methyl}-2-chloro-benzenesulfonamide (0.57 g, 1.24 mmol) dissolved in acetone (100 mL) is added Jones reagent (3 M, 0.4 mL), and the reaction mixture is stirred at room temperature for 15 minutes. The reaction is quenched with water, and the aqueous layer is extracted with methylene chloride three times. The combined organic extracts are washed with saturated sodium bicarbonate solution, a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Recrystallization from methylene chloride/hexane provides 0.28 g (50%) of the title compound as a grey solid. 1H NMR (CDCl3): δ 8.23 (d, J=2 Hz, 1H), 7.80 (dd, J=8, 2 Hz, 1H), 7.50 (d, J=8 Hz, 1H), 7.20 (m, 2H), 6.70 (d, J=8 Hz, 1H), 5.00 (s, 2H), 3.70 (s, 3H), 0.90 (s, 9H), 0.05 (s, 6H).

後処理

  1. customThe reaction is quenched with water
  2. extractionthe aqueous layer is extracted with methylene chloride three times
  3. washThe combined organic extracts are washed with saturated sodium bicarbonate solution
  4. dry with materiala saturated sodium chloride solution, dried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from methylene chloride/hexane

出典と根拠

ORDレコード
ord-9d8cf0c150fa4f3b97754688de4670bd
出典データセット
uspto-grants-2015_03
特許番号
US08975439B2

反応ノート

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