Acetic Acid → HCID 86670885, compound

HRID 2045765Notes

Reaction equation

HRID 2045765 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]([CH3:8])([CH3:7])[CH2:4][CH:3]1[C:9](=[CH2:12])[C:10]#N.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=[O:25])C.O>C1(C)C=CC=CC=1>[CH3:1][CH:2]1[CH2:6][C:5]([CH3:8])([CH3:7])[CH2:4][CH:3]1[C:9](=[CH2:12])[CH:10]=[O:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 67064808HCID 67064808, compound

Product 1

HCID 86670885HCID 86670885, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2,4,4-Trimethylcyclopentyl)acrylonitrile 5 is placed in toluene at 10° C. under an inert atmosphere. 1.2 eq. of Dibal (diisobutylaluminum hydride) are added thereto dropwise. The reaction medium is stirred at ambient temperature for a few hours and is then poured onto a 20:40:40 mixture of acetic acid, water and ice. The aqueous phase is extracted once with toluene. The combined organic phases are washed with a sodium bicarbonate solution and then with an aqueous sodium chloride solution. After drying over magnesium sulfate, filtering through paper and evaporating the solvent, the crude product, obtained in the form of two diastereomers in proportions of 70:30, is distilled under reduced pressure.

Workup

  1. extractionThe aqueous phase is extracted once with toluene
  2. washThe combined organic phases are washed with a sodium bicarbonate solution
  3. dry with materialAfter drying over magnesium sulfate
  4. filtrationfiltering through paper
  5. customevaporating the solvent

Sources & evidence

ORD record
ord-c69ee6fe2aed4e218784f8e3a85fefd6
Source dataset
uspto-grants-2013_11
Patent number
US08592360B2

Reaction notes

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