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

HRID 916018노트

반응식

HRID 916018 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 578098304-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol수율 72.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ac08c0399094a7da8025e3e3ce2d070
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268152B2

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