Iodine → 2-Iodofuran-3-carboxylic acid

HRID 1750322ノート

反応式

HRID 1750322 の反応式
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.[Li]CCCC.[I:14]I.O>O1CCCC1>[I:14][C:2]1[O:1][CH:5]=[CH:4][C:3]=1[C:6]([OH:8])=[O:7]

参加物

6

反応物 4

HCID 807IodineHCID 962WaterHCID 102683-Furoic acidHCID 178418339Butyllithium

生成物 1

HCID 685630822-Iodofuran-3-carboxylic acid収率 59%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirring solution of furan-3-carboxylic acid (5 g, 44.6 mmol) in anhydrous tetrahydrofuran (200 ml) under a nitrogen atmosphere at −78° C. was added BuLi (44.6 ml, 112 mmol) dropwise. After stirring for 0.5 h, cooling was switched off and the mixture allowed to warm to room temperature. During warming, iodine (12.5 g, 49.1 mmol) as a solution in anhydrous tetrahydrofuran (30 ml) and added dropwise to the stirring mixture. Water was added (100 ml) and the organic solvents were removed in vacuo. The aqueous solution was acidified to ca pH 1 using 2M hydrochloric acid (aq) solution (ca 10-20 ml). The precipitated solid was collected by filtration and dried under vacuum and flowing nitrogen for 16 h to afford the title compound (6.21 g, 59%) that was used in the next step without further purification. LCMS RT=0.78 min, M−H−=236.8.

後処理

  1. temperaturecooling
  2. temperatureDuring warming
  3. customthe organic solvents were removed in vacuo
  4. filtrationThe precipitated solid was collected by filtration
  5. customdried under vacuum
  6. customfor 16 h

出典と根拠

ORDレコード
ord-0228e03bae034da181e4bed1a9295070
出典データセット
uspto-grants-2015_10
特許番号
US09156853B2

反応ノート

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