Sodium Cyanide → HCID 12422087, compound

HRID 1763425Notes

Reaction equation

HRID 1763425 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. Infrared absorption spectrum (neat)

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-8f56969dd24846e58a9bcb03340868f2
Source dataset
uspto-grants-1978_09
Patent number
US04111997

Reaction notes

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