Aluminium lithium hydride → HCID 12094380, compound

HRID 2119730Notes

Reaction equation

HRID 2119730 reaction equation
C([O:4][C:5]1[C:6]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:7][C:8]2[O:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]=2[C:15]=1[CH3:16])(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:17]([C:6]1[C:5]([OH:4])=[C:15]([CH3:16])[C:9]2[CH2:10][C:11]([CH3:13])([CH3:14])[O:12][C:8]=2[CH:7]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23442880HCID 23442880, compound

Product 1

HCID 12094380HCID 12094380, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, 65 mg of 5-acetoxy-6-t-butyl-2,2,4-trimethyl-2,3-dihydrobenzofuran was dissolved in 1.5 ml of anhydrous tetrahydrofuran, a solution of 22 mg of lithium aluminium hydride in 1 ml of anhydrous tetrahydrofuran was added, and the mixture 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 solution was combined with 10% hydrochloric acid and extracted with ethyl acetate. The organic layers were washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was recrystallized from hexane to give 25 mg of 6-t-butyl-5-hydroxy-2,2,4-trimethyl-2,3-dihydrobenzofuran as a white solid (yield 45%).

Workup

  1. temperatureAfter cooling to 0° C
  2. customthe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layers were washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was recrystallized from hexane

Sources & evidence

ORD record
ord-e20438ee77884145857482b2f5d090b7
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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