Acetic Acid → HCID 86670884, compound

HRID 2045764Notes

Reaction equation

HRID 2045764 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]([CH3:8])([CH3:7])[CH2:4][CH:3]1[CH2:9][C:10]#N.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=[O:24])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[CH2:9][CH:10]=[O:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 67065089HCID 67065089, compound

Product 1

HCID 86670884HCID 86670884, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2,4,4-Trimethylcyclopentyl)acetonitrile 4 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 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-88c3e37b569e47a7ae26d06b9034ffe4
Source dataset
uspto-grants-2013_11
Patent number
US08592360B2

Reaction notes

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