Diisobutylaluminumhydride → HCID 23442890, compound

HRID 2119719Notes

Reaction equation

HRID 2119719 reaction equation
[C:1]([C:5]1[C:14]([O:15]C(=O)C(C)(C)C)=[CH:13][C:8]2[CH2:9][CH:10]([CH3:12])[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:14]([OH:15])=[CH:13][C:8]2[CH2:9][CH:10]([CH3:12])[O:11][C:7]=2[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 23442893HCID 23442893, compound

Product 1

HCID 23442890HCID 23442890, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Under a nitrogen stream, 0.15 g of 6-t-butyl-2-methy-5-trimethylacetoxy-2,3-dihydrobenzofuran was dissolved in 3 ml of n-hexane at room temperature, 1.55 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 0.09 g of 6-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran as a white solid (yield 84%).

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-872efd7dfb2e4a409a08bf9ab945803d
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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