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 1810166ノート

反応式

HRID 1810166 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. customis 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-d2cea7b4632a4c6ab4a01ef93ae65758
出典データセット
uspto-grants-2013_01
特許番号
US08362063B2

反応ノート

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