Aluminium lithium hydride → 4-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol

HRID 2106037ノート

反応式

HRID 2106037 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH2:12][C:13]([C:16]1[C:24]2[O:23][CH2:22][CH2:21][C:20]=2[CH:19]=[C:18]([Br:25])[CH:17]=1)([CH3:15])[CH3:14])C>C1COCC1>[Br:25][C:18]1[CH:17]=[C:16]([C:13]([CH3:15])([CH3:14])[CH2:12][C:11]([C:26]([F:29])([F:27])[F:28])([OH:30])[CH2:10][OH:9])[C:24]2[O:23][CH2:22][CH2:21][C:20]=2[CH:19]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 589599534-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester

生成物 1

HCID 578098304-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol収率 72.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 1.25 g (33 mmol) of lithium aluminum hydride in 50 nL of THF at 0° C. was added dropwise a solution of 11.7 g (27.5 mmol) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester in 20 mL of THF. The reaction was warmed to room temperature, stirred 2 hours, cooled to 0° C., carefully quenched with water, followed by 1N HCl, and extracted with EtOAc. The organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo. The residue was triturated with hexanes and the solid collected by filtration to afford 7.6 g (72%) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol.

後処理

  1. temperaturecooled to 0° C.
  2. customcarefully quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with hexanes
  7. filtrationthe solid collected by filtration

出典と根拠

ORDレコード
ord-bcba497bd28d491890a085df9962b9e3
出典データセット
uspto-grants-2009_08
特許番号
US07579469B2

反応ノート

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