Diisobutylaluminumhydride → HCID 13559065, compound

HRID 2229228Notes

Reaction equation

HRID 2229228 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11]/[C:12](=[CH:17]\[C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)/[C:13](OC)=[O:14]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:11]/[C:12](=[CH:17]\[C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)/[CH2:13][OH:14]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 101139664HCID 101139664, compound

Product 1

HCID 13559065HCID 13559065, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of diisobutylaluminum hydride in toluene (1.5M, 26 ml) was added dropwise to a solution of methyl (E)-2-methyl-3-(2-naphthyl)acrylate (3.52 g) in CH2Cl2 (100 ml) at −78° C. and the mixture was stirred at −78° C. for 1 hour. The mixture was washed with 1N HCl and brine, dried and concentrated. The residue was crystallized from CH2Cl2-hexane to give the titled compound (2.89 g) as a white solid.

Workup

  1. washThe mixture was washed with 1N HCl and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was crystallized from CH2Cl2-hexane

Sources & evidence

ORD record
ord-b18971b2c9134886ad570ad2e7b3e821
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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