Ammonium Chloride → (E)-3-(6-methyl-2-naphthyl)-2-buten-1-ol

HRID 2229245Notes

Reaction equation

HRID 2229245 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17](/[C:22](/[CH3:29])=[CH:23]/[C:24](OCC)=[O:25])[CH:16]=[CH:15]2.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1>[CH3:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17](/[C:22](/[CH3:29])=[CH:23]/[CH2:24][OH:25])[CH:16]=[CH:15]2

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 86758349ethyl (E)-3-(6-methyl-2-naphthyl)crotonate

Product 1

HCID 18467042(E)-3-(6-methyl-2-naphthyl)-2-buten-1-olYield 84.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of diisobutylaluminum hydride in toluene (1.5M, 30 ml) was added dropwise to a solution of ethyl (E)-3-(6-methyl-2-naphthyl)crotonate (3.62 g) in THF (50 ml) at −78° C. and the mixture was stirred at −78° C. for 15 minutes. Saturated aqueous solution of NH4Cl was added to the mixture and organic layer was washed with 1N HCl and brine, dried and concentrated. The residue was crystallized from hexane-cyclohexane gave the titled compound (2.54 g) as a colorless solid.

Workup

  1. washwas washed with 1N HCl and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was crystallized from hexane-cyclohexane

Sources & evidence

ORD record
ord-9588ffe7f37e4c1986c2b8f8b9438f10
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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