Nitroethane → HCID 178446908, compound

HRID 1658896Notes

Reaction equation

HRID 1658896 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].[OH-].C([N+](C)(C)C)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10]C=1.[C:18]([C-:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1)(=[O:21])[CH:19]=[CH2:20].[CH-]1C=CC=C1.[Fe+2:32]>C(O)C>[N+:1]([CH:4]([CH3:5])[CH2:20][CH2:19][C:18]([C-:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1)=[O:21])([O-:3])=[O:2].[CH-:10]1[CH:11]=[CH:12][CH:13]=[CH:8]1.[Fe+2:32]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 66854Benzyltrimethylammonium hydroxideHCID 178458219HCID 178458219, compound

Product 1

HCID 178446908HCID 178446908, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Nitroethane (3g; 40 m mole) in ethanol (120 ml) was heated under reflux and under nitrogen for 10 minutes with benzyltrimethyl ammonium hydroxide (1 ml) and then cooled to room temperature. Acryloylferrocene (6.5g; 27.1 mole) was then added and the solution was stirred for 1 hour and then filtered. The filtrate was concentrated on the rotary evaporator, then poured into water and extracted with chloroform. The organic extract was washed (water) and dried (sodium sulphate) to give a brown solid which was recrystallised from cyclohexane/petroleum ether to give 4-nitropentanoyl ferrocene (1.65g; 19.2%) mp 79°-80°.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated on the rotary evaporator
  3. additionpoured into water
  4. extractionextracted with chloroform
  5. extractionThe organic extract
  6. washwas washed (water)
  7. dry with materialdried (sodium sulphate)
  8. customto give a brown solid which
  9. customwas recrystallised from cyclohexane/petroleum ether

Sources & evidence

ORD record
ord-2d33208e1b9e48c7ab59e730dedcdacd
Source dataset
uspto-grants-1976_06
Patent number
US03966783

Reaction notes

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