Tetrahydrofuran → HCID 15487496, compound

HRID 278040Notes

Reaction equation

HRID 278040 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([CH3:16])[C:7]([CH3:15])=[C:8]([CH3:14])[C:9]=2[CH3:13])[CH:4]=1)#N.[H-].C([Al+]CC(C)C)C(C)C.[O:27]1CCCC1>CCCCCC>[CH3:13][C:9]1[C:8]([CH3:14])=[C:7]([CH3:15])[C:6]([CH3:16])=[C:5]2[C:10]=1[CH:11]=[CH:12][C:3]([CH:1]=[O:27])=[CH:4]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 22627634HCID 22627634, compound

Product 1

HCID 15487496HCID 15487496, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Under nitrogen atmosphere, 0.8 g of 2-cyano-5,6,7,8-tetramethylnaphthalene was dissolved in 30 ml of tetrahydrofuran, and 5.7 ml of a 1.0M solution of diisobutylaluminum hydride in hexane was added to the resulting solution at 0° C. The resulting mixture was stirred at room temperature for 2.5 hours, quenched with methanol and a saturated aqueous solution of ammonium chloride successively, and extracted with ethyl acetate (50 ml×2). The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and filtered. The resulting filtrate was concentrated and the resulting crude product was purified by silica gel column chromatography to give 0.68 g of the title compound as an oil.

Workup

  1. customquenched with methanol
  2. extractiona saturated aqueous solution of ammonium chloride successively, and extracted with ethyl acetate (50 ml×2)
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe resulting filtrate was concentrated
  7. customthe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-420e3f5f8ca048d99e4f20e9e1a2904a
Source dataset
uspto-grants-2002_03
Patent number
US06358995B1

Reaction notes

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