Sodium hydride → HCID 19082134, compound

HRID 265293Notes

Reaction equation

HRID 265293 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH:12]([C:15]#[N:16])[C:13]#[N:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:20][CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1>CS(C)=O>[O:23]1[CH2:24][CH2:25][O:26][CH:22]1[CH2:21][CH2:20][C:12]([CH2:11][CH2:10][O:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:13]#[N:14])[C:15]#[N:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 19082251HCID 19082251, compound

Product 1

HCID 19082134HCID 19082134, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of the compound from step b) (1.53 g) in dry dimethyl sulphoxide (20 ml) was added to a suspension of sodium hydride (prewashed with diethyl ether) in dimethyl sulphoxide (20 ml). The mixture was stirred for 2 hours at room temperature. 2-[2-Bromoethyl]-1,3-dioxolane (0.920 ml) was then added and the whole heated at 60° for a further 2 hours. The cooled mixture was then quenched with water, acidified with dilute aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure to yield the crude final product. This material was purified by flash chromatography over silica using ethyl acetate in dichloromethane as eluant to yield a pure sample of the subtitled compound (0.56 g, 25%).

Workup

  1. temperaturethe whole heated at 60° for a further 2 hours
  2. customThe cooled mixture was then quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto yield the crude final product
  8. customThis material was purified by flash chromatography over silica

Sources & evidence

ORD record
ord-de9a55968cf54fd79375f458475772b3
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

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