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

HRID 461397

Reaction equation

HRID 461397 reaction equation
[Na].[C:2]([S:5][CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]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 22441681HCID 22441681, compound

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 (.060 gram atom) metallic sodium. When the reaction was completed 10.2 g ( b .060 mole) of 3-acetylmercaptocycloheptane 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 (.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 lN HC1 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. additionwas added
  2. temperatureto reflux for 15 minutes
  3. temperatureThe solution was then cooled to 0°
  4. customwas partitioned between lN HC1 and methylene chloride
  5. extractionThe aqueous phase was further extracted with methylene chloride
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-fd65037503514aa684a194251a62a018
Source dataset
uspto-grants-1977_12
Patent number
US04062868

Linked notes

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