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

HRID 487314Notes

Reaction equation

HRID 487314 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×

Conditions

Temperature
5 °C

Procedure

When R2 was H, the 3-(2-nitroethenyl)thiophene (1 eq) was suspended in hexane, cooled to 5° C. in an ice bath under nitrogen and slowly treated with 2N trimethylaluminum in hexane (2.6 eq). After 30 min, 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 CH2Cl2. The product was obtained as a colorless oil (80%); MH+ at m/z 172.

Workup

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

Sources & evidence

ORD record
ord-378bf1916669437f84ca5c4c053f01c7
Source dataset
uspto-grants-1994_03
Patent number
US05294621

Reaction notes

Loading…