3-(2-Nitrovinyl)thiophene → HCID 53948007, compound

HRID 247900Notes

Reaction equation

HRID 247900 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)([O-:3])=[O:2].[CH3:11][Al](C)C>CCCCCC>[N+:1]([CH2:4][CH:5]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)[CH3:11])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 27324183-(2-Nitrovinyl)thiopheneHCID 16682925Trimethylaluminum

Product 1

HCID 53948007HCID 53948007, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

When R2 is H the 3-(2-nitroethenyl)thiophene (1 eq) was suspended in hexane, cooled in an ice bath under nitrogen and slowly treated with 2N trimethylaluminum in hexane (2.6 eq). After 30 minutes, the solution was quenched with 3N HCl, diluted with ether and filtered. The organic layer was dried (Na2SO4) and condensed under reduced pressure to afford the crude product. This material was purified by flash silica gel column chromatography using 70% hexane in methylene chloride. The product was obtained as a colorless oil (80%); MH+ at m/z 172.

Workup

  1. temperaturecooled in an ice bath under nitrogen
  2. customthe solution was quenched with 3N HCl
  3. additiondiluted with ether
  4. filtrationfiltered
  5. customThe organic layer was dried
  6. custom(Na2SO4) and condensed under reduced pressure
  7. customto afford the crude product
  8. customThis material was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-9c7146b76d414680b870c625012e4bba
Source dataset
uspto-grants-1993_05
Patent number
US05208252

Reaction notes

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