Tetrahydrofuran → HCID 69677214, compound

HRID 1900530Notes

Reaction equation

HRID 1900530 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:7][C:8]2[O:12][C:11]([CH2:14][CH2:15]/[CH:16]=[C:17](/[C:19](OCC)=[O:20])\[CH3:18])([CH3:13])[CH2:10][C:9]=2[C:24]=1[C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:3])[CH3:2].O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:7][C:8]2[O:12][C:11]([CH2:14][CH2:15]/[CH:16]=[C:17](\[CH3:18])/[CH2:19][OH:20])([CH3:13])[CH2:10][C:9]=2[C:24]=1[C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 22918661HCID 22918661, compound

Product 1

HCID 69677214HCID 69677214, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-Acetoxy-4,6-di-tert-butyl-2-(4-ethoxycarbonyl-4-methyl-3(E)-butenyl)-2-methyl-2,3-dihydrobenzofuran (13.2 g) was dissolved in benzene (250 ml) and a tetrahydrofuran solution (60 ml) of 1M diisobutylaluminum hydride was added dropwise to the solution under cooling with ice. After stirring the mixture for 1 h, a saturated aqueous solution of ammonium chloride was added and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (33% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2-(5-hydroxy-4-methyl-3(E)-pentenyl)-2-methyl-2,3-dihydrobenzofuran [3.9 g (yield, 33%)] as a colorless oil. In addition, 4,6-di-tert-butyl-5-hydroxy-2-(5-hydroxy-4-methyl-3(E)-pentenyl)-2-methyl-2,3-dihydrobenzofuran [4.2 g (yield, 39%)] was obtained as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. extractionthe mixture was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel chromatography (33% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-08af3c8e9c514d369ec7e4de31b2618f
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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