Hydrochloric Acid → HCID 15485720, compound

HRID 367293Notes

Reaction equation

HRID 367293 reaction equation
C([O:4][C:5]1[C:6]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:7][C:8]2[O:12][C:11]([CH2:14][OH:15])([CH3:13])[CH2:10][C:9]=2[C:16]=1[C:17]([CH3:20])([CH3:19])[CH3:18])(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>O1CCCC1>[C:17]([C:16]1[C:9]2[CH2:10][C:11]([CH2:14][OH:15])([CH3:13])[O:12][C:8]=2[CH:7]=[C:6]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]=1[OH:4])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 154857195-Acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 15485720HCID 15485720, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of 500 mg of 5-acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran in 7 ml of tetrahydrofuran was added dropwise to a suspension of 114 mg of lithium aluminum hydride in 3 ml of tetrahydrofuran. The mixture was heated under reflux for 2 hours and then cooled to room temperature. Ethyl acetate was added dropwise and then 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated, and the concentrate was purified by silica gel column chromatography eluting with n-hexane containing 20% ethyl acetate to give 320 mg of 4,6-di-t-butyl-5-hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran as a white solid (yield 73%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customthe concentrate was purified by silica gel column chromatography
  7. washeluting with n-hexane containing 20% ethyl acetate

Sources & evidence

ORD record
ord-2e0a0e00a84c4ff783f49c16ea9949c8
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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