Sodium → 3-[(2-Nitroethyl)sulfanyl]cyclohept-1-ene

HRID 1703459Notes

Reaction equation

HRID 1703459 reaction equation
[Na].[C:2]([S:5][CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]1)(=O)[CH3:3].[N+:13](CCOC(=O)C)([O-:15])=[O:14]>C(O)C>[N+:13]([CH2:3][CH2:2][S:5][CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 118153992-nitroethyl AcetateHCID 126209593-Acetylmercaptocycloheptene

Product 1

HCID 126210093-[(2-Nitroethyl)sulfanyl]cyclohept-1-eneYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To 40 ml of absolute ethanol was added 1.38 g (0.060 gram atom) metallic sodium. When the reaction was completed, 10.2 g (0.060 mole) of 3-acetylmercaptocycloheptene in 20 ml of absolute ethanol was added and the reaction mixture was brought up to reflux for 15 minutes. The solution was then cooled to 0° and 7.98 g (0.060 mole) of 1-nitro-2-acetoxyethane in 20 ml absolute ethanol was added. The reaction was allowed to proceed for 3.0 hours at 0° and then was partitioned between 1N HCl and methylene chloride. The aqueous phase was further extracted with methylene chloride. The organic phases were pooled, dried over sodium sulfate, and evaporated to afford 12 g (99%) of pure 3-[2-nitroethylthio]cycloheptene as a colorless oil.

Workup

  1. temperatureto reflux for 15 minutes
  2. temperatureThe solution was then cooled to 0°
  3. customwas partitioned between 1N HCl and methylene chloride
  4. extractionThe aqueous phase was further extracted with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-9c9e407c33794b408d3274b85d87cc29
Source dataset
uspto-grants-1978_11
Patent number
US04124595

Reaction notes

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