Acetic Acid → Thiophene, 2-(2-nitroethyl)-

HRID 1018989Notes

Reaction equation

HRID 1018989 reaction equation
[BH4-].[Na+].[N+:3]([CH:6]=[CH:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)([O-:5])=[O:4].C(O)(=O)C>C(Cl)(Cl)Cl.C(O)(C)C>[N+:3]([CH2:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 955862-(2-Nitro-vinyl)-thiopheneHCID 4311764Sodium borohydride

Product 1

HCID 11105610Thiophene, 2-(2-nitroethyl)-

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

15.7 g of silica 60 (230-400 mesh) and then 2.95 g of NaBH4 are added to a solution of 32.2 mmol of 2-(2-nitrovinyl)thiophene in 210 ml of chloroform and 70 ml of isopropanol. After stirring the mixture for one hour at ambient temperature, 5 ml of acetic acid are added dropwise and then, after 15 minutes, the resulting suspension is filtered and subsequently rinsed with dichloromethane. Concentration of the filtrate under reduced pressure enables the expected product to be isolated.

Workup

  1. waitafter 15 minutes
  2. filtrationthe resulting suspension is filtered
  3. washsubsequently rinsed with dichloromethane
  4. customto be isolated

Sources & evidence

ORD record
ord-a611682c5e9e4b0baedd161548830046
Source dataset
uspto-grants-2002_11
Patent number
US06486171B2

Reaction notes

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