Diisobutylaluminumhydride → HCID 9925575, compound

HRID 2119696Notes

Reaction equation

HRID 2119696 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([C:15]1[C:20]2[CH2:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=2[C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:17][C:16]=1[O:30]C(=O)C(C)(C)C)([CH3:14])([CH3:13])[CH3:12]>CCCCCC>[C:11]([C:15]1[C:20]2[CH2:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=2[C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:17][C:16]=1[OH:30])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 53674989HCID 53674989, compound

Product 1

HCID 9925575HCID 9925575, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Under a nitrogen stream, 3.60 ml of diisobutylaluminium hydride (IM in n-hexane) was added dropwise into a solution of 0.43 g of 4,7-di-t-butyl-2,2-dimethyl-5-trimethylacetoxy-2,3-dihydrobenzofuran in 5 ml of n-hexane at room temperature, and the mixture was stirred overnight. After the reaction was quenched with 5% hydrochloric acid, the reaction solution 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 0.2%-1% ethyl acetate) to give 0.22 g of 4,7-di-t-butyl-5-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran as a white solid (yield 67%).

Workup

  1. customAfter the reaction was quenched with 5% hydrochloric acid
  2. extractionthe reaction solution 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 0.2%-1% ethyl acetate)

Sources & evidence

ORD record
ord-de1664a3a078425d985b6bd8d7e35be5
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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