Water → HCID 15711992, compound

HRID 2292045Notes

Reaction equation

HRID 2292045 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[C:9]([C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][C:16]([CH3:23])([CH3:22])[CH:17]3O[CH:18]32)=[CH:13][CH:12]=1)#[N:10].O>CS(C)=O>[C:9]([C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][C:16]([CH3:23])([CH3:22])[CH:17]=[C:18]2[N:3]2[CH2:7][CH2:6][CH2:5][C:4]2=[O:8])=[CH:13][CH:12]=1)#[N:10]

Participants

6

Reactant 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 15711990HCID 15711990, compound

Product 1

HCID 15711992HCID 15711992, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a suspension of sodium hydride (0.18 g of 80% dispersion in oil) in dry dimethylsulphoxide (5 ml) was added 2-pyrrolidinone (0.51 g) in dimethylsulphoxide (5 ml) and the mixture was then stirred at room temperature, under nitrogen, for 1 hour. A solution of 7-cyano-1,2-epoxy-3,3-dimethyl-1,2,3,4,-tetrahydronaphthalene (1.0 g) in dimethylsulphoxide was then added dropwise, and the solution stirred for 18 hours at room temperature. The mixture was then poured into water and extracted into ethyl acetate. The combined organic layers were washed with water, then brine, and dried over sodium sulphate. Removal of drying agent and solvent, followed by chromatography of the residue on a silica gel column eluted with ethyl acetate-pentane (1:1), gave the title compound as a solid, which recrystallised from 60°-80° petrol-ethyl acetate (5:1) as yellow prisms (0.25 g) having mp 131°-2° C.;

Workup

  1. stirringthe solution stirred for 18 hours at room temperature
  2. extractionextracted into ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialbrine, and dried over sodium sulphate
  5. customRemoval
  6. customof drying agent and solvent
  7. washeluted with ethyl acetate-pentane (1:1)

Sources & evidence

ORD record
ord-857a12d39cb24ffeae39e9407c122c6e
Source dataset
uspto-grants-1989_01
Patent number
US04800212

Reaction notes

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