HCID 12094379, compound → HCID 12094378, compound

HRID 2119723Notes

Reaction equation

HRID 2119723 reaction equation
C([O:4][C:5]1[C:6]([CH:21]([CH3:23])[CH3:22])=[CH:7][C:8]2[O:12][C:11]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:10][C:9]=2[C:17]=1[CH:18]([CH3:20])[CH3:19])(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:15]([C:11]1([CH2:13][CH3:14])[CH2:10][C:9]2[C:17]([CH:18]([CH3:20])[CH3:19])=[C:5]([OH:4])[C:6]([CH:21]([CH3:23])[CH3:22])=[CH:7][C:8]=2[O:12]1)[CH3:16]

Participants

4

Reactant 2

HCID 12094379HCID 12094379, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12094378HCID 12094378, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, 432 mg of 5-acetoxy-2,2-diethyl-4,6-diisopropyl-2,3-dihydrobenzofuran was dissolved in 3 ml of anhydrous tetrahydrofuran, a solution of 129 mg of lithium aluminium hydride in 2 ml of anhydrous tetrahydrofuran was added, and the solution was stirred at room temperature for 6 hours. After the reaction was quenched with water, the reaction solution was combined with 10% hydrochloric acid and extracted with 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 376 mg of 2,2-diethyl-5-hydroxy-4,6-diisopropyl-2,3-dihydrobenzofuran as a light brown solid (yield 100%).

Workup

  1. customAfter the reaction was quenched with water
  2. extractionextracted with 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 by silica gel column chromatography (in n-hexane containing 1% ethyl acetate)

Sources & evidence

ORD record
ord-2bc3b8f7e56345e5bd1190b04d3004b5
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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