Diisobutylaluminumhydride → HCID 14296006, compound

HRID 2186288Notes

Reaction equation

HRID 2186288 reaction equation
[C:1]([C:5]1[C:13]([O:14]C(=O)C(C)(C)C)=[CH:12][C:8]2[CH:9]=[CH:10][O:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>CCCCCC>[C:1]([C:5]1[C:13]([OH:14])=[CH:12][C:8]2[CH:9]=[CH:10][O:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 54345064HCID 54345064, compound

Product 1

HCID 14296006HCID 14296006, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Under a nitrogen stream, 0.12 g of 6-t-butyl-5-trimethylacetoxybenzofuran was dissolved in 5 ml of n-hexane at room temperature and 1.31 ml of diisobutylaluminium hydride (1M in n-hexane) was added dropwise and the mixture was stirred overnight. After the reaction was quenched with 5% hydrochloric acid, the mixture was extracted with water and ethyl acetate. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified on a short column of silica gel (in n-hexane containing 5% ethyl acetate) to give 0.07 g of 6-t-butyl-5-hydroxybenzofuran as a reddish brown oil.

Workup

  1. customAfter the reaction was quenched with 5% hydrochloric acid
  2. extractionthe mixture was extracted with water and ethyl acetate
  3. washThe organic layers were washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified on a short column of silica gel (in n-hexane containing 5% ethyl acetate)

Sources & evidence

ORD record
ord-76e929c2f675470288c0c77a87174185
Source dataset
uspto-grants-2002_06
Patent number
US06403639B1

Reaction notes

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