Water → HCID 19009244, compound

HRID 1742500Notes

Reaction equation

HRID 1742500 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH2:15][CH2:16][CH2:17]I.[C-:19]#[N:20].[Na+].O>CS(C)=O>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH2:15][CH2:16][CH2:17][C:19]#[N:20]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 19009258HCID 19009258, compound

Product 1

HCID 19009244HCID 19009244, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5.08 g of 3-(1,4-dimethoxy-2-naphthyl)propyl iodide (prepared as described in Preparation 30), and 0.70 g of sodium cyanide in 60 ml of dry dimethyl sulfoxide was stirred at 60° C. (external temperature) for 80 minutes. At the end of this time, the reaction mixture was cooled and poured into water, after which it was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.36 g of the title compound as a colorless oil.

Workup

  1. temperatureAt the end of this time, the reaction mixture was cooled
  2. extractionafter which it was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-7e66163b5f224d7085917d579da18464
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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