HCID 18349870, compound → HCID 22091595, compound

HRID 2229243Notes

Reaction equation

HRID 2229243 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1([CH3:32])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16](/[C:24](/[CH3:31])=[CH:25]/[C:26](OCC)=[O:27])[CH:15]=[CH:14][C:13]1=2>C1(C)C=CC=CC=1.C1COCC1>[CH3:11][C:12]1([CH3:32])[CH2:21][CH2:20][C:19]([CH3:22])([CH3:23])[C:18]2[CH:17]=[C:16](/[C:24](/[CH3:31])=[CH:25]/[CH2:26][OH:27])[CH:15]=[CH:14][C:13]1=2

Participants

5

Reactant 2

HCID 18349870HCID 18349870, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 22091595HCID 22091595, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diisobutylaluminum hydride in toluene (1.5M, 50 ml) was added dropwise to a solution of ethyl (E)-3-(5,5,8,8,-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)crotonate (6.30 g) in THF (100 ml) at −78° C. and the mixture was stirred at −78 0° C. for 15 minutes. The mixture was washed with 1N HCl and brine, dried and concentrated. The residue was chromatographed on silica gel (hexane-ethyl acetate=10:1) to give the titled compound (4.33 g) as a colorless oil.

Workup

  1. washThe mixture was washed with 1N HCl and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (hexane-ethyl acetate=10:1)

Sources & evidence

ORD record
ord-0f77e8368f674a0f94d55e821c34cc1f
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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