Hydrochloric Acid → 4-Cyano-4-(3-cyano-5-thienyl)-5-methylhexanol

HRID 1071625Notes

Reaction equation

HRID 1071625 reaction equation
[C:1]([C:3]([C:14]1[S:18][CH:17]=[C:16]([C:19]#[N:20])[CH:15]=1)([CH:11]([CH3:13])[CH3:12])[CH2:4][CH2:5][C:6](OCC)=[O:7])#[N:2].[BH4-].[Li+].Cl.O>C1COCC1>[C:1]([C:3]([C:14]1[S:18][CH:17]=[C:16]([C:19]#[N:20])[CH:15]=1)([CH:11]([CH3:13])[CH3:12])[CH2:4][CH2:5][CH2:6][OH:7])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 22393597Ethyl 4-cyano-4-(3-cyano-5-thienyl)-5-methylhexanate

Product 1

HCID 223935934-Cyano-4-(3-cyano-5-thienyl)-5-methylhexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-cyano-4-(3-cyano-5-thienyl)-5-methylhexanate (0.55 g) was dissolved in THF (10 ml), lithium borohydride (46 mg) was added, and the mixture was heated under reflux for 1.5 hours. After cooling as it was to room temperature, 1N aqueous hydrochloric acid and water were added at 0° C., and the mixture was extracted with ethyl acetate. The mixture was further washed with brine, dried over anhydrous magnesium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system), to give the title compound pale as a yellow oil (1.25 g, 47%). Further, the catalyst was filtered off, and the filtrate was evaporated. The resulting residue was purified by preparative thin layer silica gel column chromatography (hexane/ethyl acetate system), to give the title compound as a pale yellow oil (0.39 g, 83%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling as it
  4. customwas to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe mixture was further washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-b235a9e760fc4c7299c81c7bef341694
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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