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Diisobutylaluminumhydride toluene → [2-Fluoro-3-({[2-(morpholin-4-yl)pyrimidin-5-yl]oxy}methyl)phenyl]methanol

HRID 2171644
ノート
印刷プレビュー

反応式

HRID 2171644 の反応式
[F:1][C:2]1[C:12]([CH2:13][O:14][C:15]2[CH:16]=[N:17][C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:19][CH:20]=2)=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](OCC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[C:12]([CH2:13][O:14][C:15]2[CH:16]=[N:17][C:18]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[N:19][CH:20]=2)=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][OH:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 86583787Diisobutylaluminumhydride tolueneHCID 86686214Ethyl 2-fluoro-3-({[2-(morpholin-4-yl)pyrimidin-5-yl]oxy}methyl)benzoate

生成物 1

HCID 68309834[2-Fluoro-3-({[2-(morpholin-4-yl)pyrimidin-5-yl]oxy}methyl)phenyl]methanol収率 85.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

Ethyl 2-fluoro-3-({[2-(morpholin-4-yl)pyrimidin-5-yl]oxy}methyl)benzoate (375 mg) was mixed with toluene (5 ml), followed by cooling to 0° C. A 1.01 M diisobutylaluminum hydride/toluene solution (3 ml) was added dropwise thereto, followed by stirring at the same temperature for 1 hour. The reaction mixture was subjected to liquid separation by the addition of a 1 M aqueous NaOH solution and toluene. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain [2-fluoro-3-({[2-(morpholin-4-yl)pyrimidin-5-yl]oxy}methyl)phenyl]methanol (282 mg).

後処理

  1. customThe reaction mixture was subjected to liquid separation by the addition of a 1 M aqueous NaOH solution and toluene
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-e671b2099153434badf29dc06d45c01a
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09051283B2

反応ノート

読み込み中…

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