Acetic Acid → HCID 86670886, compound

HRID 2045766Notes

Reaction equation

HRID 2045766 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]([CH3:8])([CH3:7])[CH2:4][CH:3]1[CH:9]([CH3:12])[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[CH:9]([CH3:12])[CH:10]=[O:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 67065300HCID 67065300, compound

Product 1

HCID 86670886HCID 86670886, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2,4,4-Trimethylcyclopentyl)propanenitrile 6 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 three diastereomers observed by GC in proportions of 73:16:11, 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-b77563f86cfe4f51986a961cd28c5e71
Source dataset
uspto-grants-2013_11
Patent number
US08592360B2

Reaction notes

Loading…