Ethyl Acetate → 3-Cyano-2-oxo-6-[3-(4-trifluoromethylphenyl)phenyl]heptane

HRID 1081661Notes

Reaction equation

HRID 1081661 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:15]([CH3:21])[CH2:16][CH2:17][CH2:18][C:19]#[N:20])[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.C([Li])CCC.[C:29](OCC)(=[O:31])[CH3:30]>O1CCCC1>[C:19]([CH:18]([CH2:17][CH2:16][CH:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:22])([F:23])[F:1])=[CH:8][CH:7]=2)[CH:10]=1)[CH3:21])[C:29](=[O:31])[CH3:30])#[N:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 199555515-[3-(4-Trifluoromethylphenyl)phenyl]hexanenitrileHCID 178418339Butyllithium

Product 1

HCID 199555243-Cyano-2-oxo-6-[3-(4-trifluoromethylphenyl)phenyl]heptaneYield 31.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere a stirred solution of 2.5 grams (0.008 mole) of 5-[3-(4-trifiuoromethylphenyl)phenyl]hexanenitrile in 20 mL of tetrahydrofuran was cooled to about -78 ° C., and 3.2 mL (0.008 mole) of n-butyllithium (2.5 molar in hexane) was added dropwise. Upon completion of addition, the reaction mixture was stirred at -78 ° C. for 30 minutes, and then 1.1 grams (0.012 mole) of ethyl acetate was added dropwise. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature as it stirred for about 60 hours. The reaction mixture was partitioned between ethyl acetate and aqueous dilute hydrochloric acid. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel, using 25% ethyl acetate in hexane as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding about 0.9 gram of 3-cyano-2-oxo-6-[3-(4-trifiuoromethylphenyl)phenyl]heptane. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. additionUpon completion of addition
  3. temperatureto warm to ambient temperature as it
  4. stirringstirred for about 60 hours
  5. customThe reaction mixture was partitioned between ethyl acetate and aqueous dilute hydrochloric acid
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a residue
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7408313aa0c841019451d55c7cec7531
Source dataset
uspto-grants-1996_12
Patent number
US05587379

Reaction notes

Loading…