1-Naphthaleneacetonitrile → HCID 18979205, compound

HRID 2393166Notes

Reaction equation

HRID 2393166 reaction equation
[C:1]1([CH2:11][C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C.O>[C:12]([CH:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:13]

Participants

6

Reactant 3

HCID 85961-NaphthaleneacetonitrileHCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 18979205HCID 18979205, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In 125 ml of DMF was dissolved 12.54 g (75 mmol) of 1-naphthaleneacetonitrile. Then, 3.30 g (82.5 mmol) of 60% sodium hydride was added at room temperature and the mixture was heated to 60° C. and stirred for 30 minutes. After cooling to room temperature, 13.17 ml (82.5 mmol) of ethyl 5-bromovalerate was added. The reaction was further conducted at 60° C. for 30 minutes, after which the reaction mixture was cooled to <10° C. and diluted with 500 ml of pure water. The diluted mixture was extracted with 200 ml of ethyl acetate twice and the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off and the residue was purified by silica gel column chromatography (hexane-CH2Cl2 -ethyl acetate=4:2:1) to provide 17.16 g (yield 77.5%) of the title compound as light-yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. waitThe reaction was further conducted at 60° C. for 30 minutes
  3. temperatureafter which the reaction mixture was cooled to <10° C.
  4. extractionThe diluted mixture was extracted with 200 ml of ethyl acetate twice
  5. washthe organic layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was then distilled off
  8. customthe residue was purified by silica gel column chromatography (hexane-CH2Cl2 -ethyl acetate=4:2:1)

Sources & evidence

ORD record
ord-735f47964e76444780f8121033daaf65
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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