Hydrochloric Acid → 2-Cyano-5-(naphth-1-yl)pentanenitrile

HRID 440966노트

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HRID 440966 반응식
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].[C:8]1([CH2:18][CH2:19][CH2:20]I)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.Cl>O1CCCC1.O>[C:3]([CH:2]([CH2:20][CH2:19][CH2:18][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)[C:1]#[N:5])#[N:4]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 24758Sodium hydrideHCID 199555551-(3-Iodopropyl)naphthalene

생성물 1

HCID 199555442-Cyano-5-(naphth-1-yl)pentanenitrile수율 46.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 0.7 gram (0.011 mole) of malononitrile in 50 mL of tetrahydrofuran was stirred, and 0.5 gram (0.011 mole) of sodium hydride (60% in mineral oil) was added portionwise during a ten minute period. Upon completion of addition, the reaction mixture was stirred for 30 minutes at ambient temperature. After this time a solution of 3.0 grams (0.010 mole) of 3-(naphth-1-yl)propyl iodide (prepared as in Example 9, Steps A-D) in about 5 mL of tetrahydrofuran was added in one portion. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 20 hours. The reaction mixture was acidified with aqueous 6N hydrochloric acid and then was further diluted with 100 mL of water. The mixture was extracted with two 100 mL portions of diethyl ether. The combined extracts were washed with an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated to a residue which was subjected to column chromatography on silica gel. Elution was accomplished using 40% to 65% methylene chloride and petroleum ether. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.1 grams of 2-cyano-5-(naphth-1-yl)pentanenitrile. The NMR spectrum was consistent with the proposed structure.

후처리

  1. additionUpon completion of addition
  2. additionUpon completion of addition
  3. stirringthe reaction mixture was stirred at ambient temperature for about 20 hours
  4. extractionThe mixture was extracted with two 100 mL portions of diethyl ether
  5. washThe combined extracts were washed with an aqueous solution saturated with sodium chloride
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated to a residue which
  9. washElution
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c8b7760837fa49e499264c7072d97429
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521192

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