Hydrochloric Acid → HCID 19955474, compound

HRID 440956Notes

Reaction equation

HRID 440956 reaction equation
[O:1]=[C:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=1)[CH2:3][C:4]#[N:5].[BH4-].[Na+].Cl>O1CCCC1>[OH:1][CH:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=1)[CH2:3][C:4]#[N:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 19955532HCID 19955532, compound

Product 1

HCID 19955474HCID 19955474, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere a stirred solution of 5.5 grams (0.022 mole) of 3-oxo-5-(3-phenylphenyl)pentanenitrile and 0.5 gram (0.013 mole) of sodium borohydride in 75 mL of tetrahydrofuran was heated at reflux for four hours. After this time the reaction mixture was allowed to cool to ambient temperature where it stood for about 16 hours. The reaction mixture was then poured into 300 mL of aqueous 1N hydrochloric acid. The mixture was extracted with two 150 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. NMR analysis of the residual oil indicated that it was impure. The oil was dissolved in 20:1 methylene chloride and ethyl acetate, and the solution was passed through a column of silica gel. The eluate was concentrated under reduced pressure, yielding 3.8 grams of 3-hydroxy-5-(3-phenyl-phenyl)pentanenitrile. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for four hours
  2. extractionThe mixture was extracted with two 150 mL portions of diethyl ether
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  6. dissolutionThe oil was dissolved in 20:1 methylene chloride and ethyl acetate
  7. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-df7fa350718f4d6a8981699cb1a68398
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

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