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Acetic Acid → Diisopropyl Ether

HRID 2243345
ノート
印刷プレビュー

反応式

HRID 2243345 の反応式
[F:1][C:2]1[C:25]([F:26])=[CH:24][C:5]2[NH:6][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14](=[N:22]O)[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[C:27]([OH:30])(=O)[CH3:28].[CH2:31](O)C>O.[Zn]>[CH:27]([O:30][CH:25]([CH3:24])[CH3:2])([CH3:28])[CH3:31].[F:26][C:25]1[C:2]([F:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH:14]([NH2:22])[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:6][C:5]=2[CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 176Acetic AcidHCID 702EthanolHCID 137227840HCID 137227840、化合物

生成物 2

HCID 7914Diisopropyl EtherHCID 67358643HCID 67358643、化合物

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 962Water
溶媒

実験手順

The procedure used in Example 216 is followed. In a 100 ml round-bottomed flask under an argon atmosphere, dissolve 830 mg of 4-(5,6-difluoro-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 5.5 ml of ethanol and 5.5 ml of water and 5.5 ml of acetic acid, at room temperature, add 624 mg of zinc in three stages, and, between each addition, stir for approximately one hour to two hours. Add Celite and filter. The filtrate is concentrated under pressure. The crude product is purified by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (98/2 by volume). After formation of a paste with diisopropyl ether, in this way we obtain 653 mg of 4-(5,6-difluoro-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a white powder, which is used as it is in the following stage, with the following characteristics:

後処理

  1. additionbetween each addition
  2. filtrationAdd Celite and filter
  3. concentrationThe filtrate is concentrated under pressure
  4. customThe crude product is purified by flash chromatography on silica gel (40-63 μm)
  5. washeluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (98/2 by volume)

出典と根拠

ORDレコード
ord-71711611570a446f9308e668d285605e
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07674795B2

反応ノート

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