Acetic Acid → 6-(Benzenesulphonylmethyl)-3-ethyl-2-methoxy-benzoic acid

HRID 2177666ノート

反応式

HRID 2177666 の反応式
OO.[C:3]1([S:9][CH2:10][C:11]2[C:16]([C:17]([O:19]CC)=[O:18])=[C:15]([O:22][CH3:23])[C:14]([CH2:24][CH3:25])=[CH:13][CH:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-:26].[Li+].C(O)(=[O:30])C>O1CCOCC1.O>[C:3]1([S:9]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([CH2:24][CH3:25])=[CH:13][CH:12]=2)(=[O:30])=[O:26])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 67107436Ethyl 6-(phenylthiomethyl)-3-ethyl-2-methoxybenzoate2 回

生成物 1

HCID 529138626-(Benzenesulphonylmethyl)-3-ethyl-2-methoxy-benzoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

Hydrogen peroxide (30% aqueous solution, 0.117 ml) was added to a solution of ethyl 6-(phenylthiomethyl)-3-ethyl-2-methoxybenzoate (Intermediate 19, 0.057 g) in acetic acid (1.7 ml) and the resultant solution was stirred and heated at 60° C. for 2 hours. After cooling, the solution was evaporated to dryness to give the crude sulphone. The residue was dissolved in a mixture of dioxane (1 ml) and water (1 ml) and lithium hydroxide (0.072 g) was added. The mixture was stirred and heated in the microwave at 160° C. for 15 minutes. After cooling, the mixture was evaporated to dryness and the residue was acidified by addition of hydrochloric acid (1M) and then immediately purified by preparative HPLC (C18) eluting with a mixture of methanol and water containing 0.1% formic acid to give 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxy-benzoic acid (0.022 g) as a white solid.

後処理

  1. temperatureAfter cooling
  2. customthe solution was evaporated to dryness
  3. customto give the crude sulphone
  4. additionwas added
  5. temperatureheated in the microwave at 160° C. for 15 minutes
  6. temperatureAfter cooling
  7. customthe mixture was evaporated to dryness
  8. additionthe residue was acidified by addition of hydrochloric acid (1M)
  9. customimmediately purified by preparative HPLC (C18)
  10. washeluting with a mixture of methanol and water containing 0.1% formic acid

出典と根拠

ORDレコード
ord-63061ef805dd4d969c641f917f417588
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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