Acetone → HCID 67064815, compound

HRID 2045761Notes

Reaction equation

HRID 2045761 reaction equation
[BH4-].[Na+].[C:3]([C:5](=[C:10]1[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][CH:11]1[CH3:17])[C:6](OC)=[O:7])#[N:4].CC(C)=O.Cl>C(O)C>[OH:7][CH2:6][CH:5]([CH:10]1[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][CH:11]1[CH3:17])[C:3]#[N:4]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 68226704HCID 68226704, compound

Product 1

HCID 67064815HCID 67064815, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.1 eq. of sodium borohydride are placed in ethanol at 10° C. under an inert atmosphere. Methyl 2-cyano-2-(2,4,4-tri-methylcyclopentylidene)acetate B is added thereto dropwise. The reaction medium is stirred at ambient temperature overnight and is then neutralized with acetone. It is subsequently poured onto a cold 10% HCl solution. The aqueous phase is extracted twice with MTBE. 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, 3-hydroxy-2-(2,4,4-tri-methylcyclopentyl)propanenitrile is obtained in the form of four diastereomers in the proportions of 11:13:23:53.

Workup

  1. extractionThe aqueous phase is extracted twice with MTBE
  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-05863edbd695492b828e88c16cc4f0ad
Source dataset
uspto-grants-2013_11
Patent number
US08592360B2

Reaction notes

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