Sodium Cyanide → HCID 12422087, compound

HRID 436160Notes

Reaction equation

HRID 436160 reaction equation
Cl[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]=2[CH2:5][CH2:4][CH2:3]1.[C-:17]#[N:18].[Na+]>CS(C)=O>[C:17]([CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]=2[CH2:5][CH2:4][CH2:3]1)#[N:18]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 12422086HCID 12422086, compound

Product 1

HCID 12422087HCID 12422087, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

In 44 ml. of dimethylsulfoxide is dissolved 4.4 g. of ethyl 1-chloro-1,2,3,4-tetrahydro-5-naphthoate, followed by the addition of 2 g. of sodium cyanide. The mixture is stirred at 50° C for 3 hours and following the addition of 450 ml. of 0.2N hydrochloric acid, the mixture is extracted with ethyl ether. The organic layer is washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure and the resultant oily residue is purified by column chromatography on silica gel (100 g. silica gel; eluted with benzene). The procedure gives ethyl 1-cyano-1,2,3,4-tetrahydro-5-naphthoate as an oily product.

Workup

  1. additionthe addition of 450 ml
  2. extractionof 0.2N hydrochloric acid, the mixture is extracted with ethyl ether
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe resultant oily residue is purified by column chromatography on silica gel (100 g. silica gel; eluted with benzene)

Sources & evidence

ORD record
ord-29f6fe728c524f1b81aa7f000c182e02
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

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