Water → HCID 86744805, compound

HRID 2051510Notes

Reaction equation

HRID 2051510 reaction equation
Br[CH2:2][C@H:3]1[CH2:14][C@H:13]2[C:15]3[C:9]([CH2:10][CH2:11][CH2:12]2)=[CH:8][CH:7]=[CH:6][C:5]=3[CH2:4]1.[C-:16]#[N:17].[Na+].O>CS(C)=O>[CH2:4]1[C:5]2=[C:15]3[C:9](=[CH:8][CH:7]=[CH:6]2)[CH2:10][CH2:11][CH2:12][C@H:13]3[CH2:14][C@@H:3]1[CH2:2][C:16]#[N:17]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 86744806HCID 86744806, compound

Product 1

HCID 86744805HCID 86744805, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1.6 g cis-2-bromomethyl-2,3,3a,4,5,6-hexahydro-1H-phenalene 13 and 330 mg NaCN in 7 ml DMSO (dimethylsulphoxide) was heated at 80°-85° C. for 4 hours. The reaction mixture was then poured into 50 ml water and the product extracted with ether. The organic layer was washed with water, dried and evaporated. This yielded 1.2 g of the nitrile 14.

Workup

  1. extractionthe product extracted with ether
  2. washThe organic layer was washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-2f63b54744434506886f21e1094ec8b6
Source dataset
uspto-grants-1991_05
Patent number
US05019585

Reaction notes

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