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

HRID 916018ノート

反応式

HRID 916018 の反応式
C([O:3][C:4](=O)[C:5]([OH:24])([C:20]([F:23])([F:22])[F:21])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[CH:13]=[C:12]([Br:19])[CH:11]=1)([CH3:9])[CH3:8])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:19][C:12]1[CH:11]=[C:10]([C:7]([CH3:9])([CH3:8])[CH2:6][C:5]([C:20]([F:23])([F:21])[F:22])([OH:24])[CH2:4][OH:3])[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[CH:13]=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 72.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the 2.28 g (5.36 mmol) of the above 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester in 30 mL of dry THF was added 705 mg (18.57 mmol) of lithium aluminum hydride in several portions. The mixture foamed and became slightly exothermic and was then warmed at reflux for 1.5 hours. The mixture was then cooled and cautiously quenched with water dropwise, dried over magnesium sulfate, filtered through diatomaceous earth, and concentrated in vacuo to afford 1.82 g of crude product as a white solid. Trituration with hexanes followed by filtration afforded 1.49 g (72%) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol as a white solid, m.p. 124° C.-128° C.

後処理

  1. temperaturewas then warmed
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe mixture was then cooled
  4. customcautiously quenched with water dropwise
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through diatomaceous earth
  7. concentrationconcentrated in vacuo
  8. customto afford 1.82 g of crude product as a white solid
  9. filtrationTrituration with hexanes followed by filtration

出典と根拠

ORDレコード
ord-5ac08c0399094a7da8025e3e3ce2d070
出典データセット
uspto-grants-2007_09
特許番号
US07268152B2

反応ノート

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