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

HRID 2106037Notes

Reaction equation

HRID 2106037 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bcba497bd28d491890a085df9962b9e3
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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