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

HRID 2106037노트

반응식

HRID 2106037 반응식
[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

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 72.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bcba497bd28d491890a085df9962b9e3
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579469B2

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