Water → HCID 53874568, compound

HRID 1081631Notes

Reaction equation

HRID 1081631 reaction equation
CS(O[CH:6]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=1)[CH2:7][C:8]#[N:9])(=O)=O.[I-].[Na+].O.C(OCC)C>COCCOC.[Zn]>[C:18]1([C:14]2[CH:13]=[C:12]([CH2:11][CH2:10][CH:6]=[CH:7][C:8]#[N:9])[CH:17]=[CH:16][CH:15]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 5238Sodium IodideHCID 19955454HCID 19955454, compound

Product 1

HCID 53874568HCID 53874568, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of 3.4 grams (0.010 mole) of 3-methylsulfonyloxy-5-(3-phenylphenyl)pentanenitrile, 3.4 grams (0.023 mole) of sodium iodide, 3.4 grams (0.052 mole) of zinc powder, and 3.4 mL of water in 50 mL of ethylene glycol dimethyl ether was heated at reflux for about 22 hours. The reaction mixture was cooled, and 150 mL of diethyl ether was added. The mixture was filtered, and the filtrate was washed in succession with water, an aqueous 5% hydrochloric acid solution, an aqueous 5% sodium bicarbonate solution, an aqueous 5% sodium bicarbonate solution, an aqueous 5% sodium thiosulfate solution, and finally with water. The organic layer was 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 10:1 petroleum ether and diethyl ether, and the solution was passed through a column of silica gel. Early fractions of eluate were combined and concentrated under reduced pressure, yielding an intermediate product, 5-(3-phenylphenyl)-2-pentenenitrile. Later fractions of the eluate were combined and concentrated under reduced pressure, yielding the intended product, 5-(3-phenylphenyl)pentanenitrile. The intermediate was hydrogenated in a manner analogous to that of Example 3, Step B, yielding an additional amount of 5-(3-phenylphenyl)pentanenitrile. All samples of the pentanenitrile were combined, yielding 1.4 grams of that product. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about 22 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe mixture was filtered
  5. washthe filtrate was washed in succession with water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  9. dissolutionThe oil was dissolved in 10:1 petroleum ether and diethyl ether
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29079a16475144dea1128e29a83af2bf
Source dataset
uspto-grants-1996_12
Patent number
US05587379

Reaction notes

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