Aluminium lithium hydride → HCID 14258220, compound

HRID 2119725Notes

Reaction equation

HRID 2119725 reaction equation
C([O:4][C:5]1[C:6]([CH:19]([CH3:21])[CH3:20])=[CH:7][C:8]2[O:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]=2[C:15]=1[CH:16]([CH3:18])[CH3:17])(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:4][C:5]1[C:6]([CH:19]([CH3:21])[CH3:20])=[CH:7][C:8]2[O:12][C:11]([CH3:13])([CH3:14])[CH2:10][C:9]=2[C:15]=1[CH:16]([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23442855HCID 23442855, compound

Product 1

HCID 14258220HCID 14258220, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, 77 mg of 5-acetoxy-2,2-dimethyl-4,6-diisopropyl-2,3-dihydrobenzofuran was dissolved in 1 ml of anhydrous tetrahydrofuran, a solution of 25 mg of lithium aluminium hydride in 2 ml of anhydrous tetrahydrofuran was added, and the solution was stirred at room temperature for a whole day and night. After cooling to 0° C., the reaction was quenched with water and then the reaction mixture was extracted with a 10% aqueous hydrochloric acid solution and ethyl acetate. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate) to give 42 mg of 5-hydroxy-2,2-dimethyl-4,6-diisopropyl-2,3-dihydrobenzofuran as a light red solid (yield 64%).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction was quenched with water
  3. extractionthe reaction mixture was extracted with a 10% aqueous hydrochloric acid solution and ethyl acetate
  4. washThe organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate)

Sources & evidence

ORD record
ord-5400efaa2a794736be502f69403c1201
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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