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

HRID 2184805Notes

Reaction equation

HRID 2184805 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-bf2bcee31d8847d9adc4f2c7f237a387
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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