Hydrochloric Acid → 4-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexanol

HRID 1071631Notes

Reaction equation

HRID 1071631 reaction equation
C([CH:3]([O-:19])[CH2:4][CH2:5][C:6]([C:17]#[N:18])([C:10]1[S:11][CH:12]=[CH:13][C:14]=1[C:15]#[N:16])[CH:7]([CH3:9])[CH3:8])C.[BH4-].[Li+].Cl>C1COCC1>[C:17]([C:6]([C:10]1[S:11][CH:12]=[CH:13][C:14]=1[C:15]#[N:16])([CH:7]([CH3:9])[CH3:8])[CH2:5][CH2:4][CH2:3][OH:19])#[N:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 22393598Ethyl 4-cyano-5-methyl-4-(3-cyano-2-thienyl)hexanolate

Product 1

HCID 223936344-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexanolYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg (1.72 mmol) of ethyl 4-cyano-5-methyl-4-(3-cyano-2-thienyl)hexanolate was dissolved in 10 ml of THF, 37.5 mg (1.72 mmol) of lithium borohydride was added, and the mixture was heated under reflux. After one hour 20 minutes, heating was stopped, and 2N HCl was added under ice-cooling. The mixture was extracted with ethyl acetate, and the extract was successively washed with brine and water, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to obtain a crude product. The crude product was subjected to silica gel (eluted with ethyl acetate:hexane=35:65), to give 244 mg (0.98 mmol, 57.1%) of the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureheating
  4. temperaturecooling
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe extract was successively washed with brine and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customto obtain a crude product

Sources & evidence

ORD record
ord-3796e69a27fb4acf8c18fe5df52a48e8
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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