Sodium Bicarbonate → (4-(Methylsulfinyl)phenyl)boronic acid

HRID 1708053ノート

反応式

HRID 1708053 の反応式
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1.C(=O)(O)[O-:13].[Na+]>C(#N)C.O>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([B:9]([OH:11])[OH:10])=[CH:7][CH:8]=1)=[O:13]

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 27339594-(Methylthio)phenylboronic acid

生成物 1

HCID 2773531(4-(Methylsulfinyl)phenyl)boronic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

A solution of [4-(methylthio)phenyl]boronic acid (1.008 g) in acetonitrile (60 ml) and water (6 ml) was cooled with a dry ice-acetone bath until it just began to freeze. A solution of ceric ammonium nitrate (6.72 g) in water (10 ml) was added with swirling. The resulting solution was left to warm to room temperature. The mixture was then basified to pH5 by addition of 8% aqueous sodium bicarbonate (16 ml) and evaporated to dryness by re-evaporation with absolute ethanol. The dried residue was purified by SPC (Merck 7729) using ethyl acetate-ethanol (9:1 followed by 4:1 and 7:3) as eluent, to give a colourless solid. The solid was further purified by FCC eluting with dichloromethane:ethanol (9:1) to give the title compound (1.00 g) as a colourless gum.

後処理

  1. waitThe resulting solution was left
  2. customevaporated to dryness by re-evaporation with absolute ethanol
  3. customThe dried residue was purified by SPC (Merck 7729)
  4. customto give a colourless solid
  5. customThe solid was further purified by FCC
  6. washeluting with dichloromethane:ethanol (9:1)

出典と根拠

ORDレコード
ord-9fd814a5c77a44f1833a60e2c7ce6128
出典データセット
uspto-grants-1994_10
特許番号
US05356893

反応ノート

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