Tetrahydrofuran → HCID 21540488, compound

HRID 1076396Notes

Reaction equation

HRID 1076396 reaction equation
[S:1]1[CH:5]=[CH:4]C=[C:2]1CC(O)=O.ClC[O:12][CH2:13][CH2:14][N+:15]([O-:17])=[O:16].[O:18]1CCCC1>N1C=CC=CC=1>[C:5]([S:1][CH2:2][O:12][CH2:13][CH2:14][N+:15]([O-:17])=[O:16])(=[O:18])[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 159702-Thiopheneacetic acidHCID 14868550HCID 14868550, compound

Product 1

HCID 21540488HCID 21540488, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thiolacetic acid (22.8 grams) and 41.7 grams of 2-chloromethoxy-1-nitroethane were mixed into 100 cc of tetrahydrofuran at room temperature and the clear solution was heated at reflux for 2 hours. The solution was cooled and 25 grams of pyridine was added. After an additional period of two hours at reflux the mixture was filtered and the solvent was removed from the filtrate by flash evaporation. The residue was taken up in ether, washed with 5 percent aqueous hydrochloric acid and water, dried over magnesium sulfate and the solvent again evaporated. Distillation in vacuo afforded 24.7 g of 2-acetylthiomethoxy-1-nitroethane, bp 106°-109° (0.2-0.5 mm); structure was confirmed by spectral analysis.

Workup

  1. temperaturethe clear solution was heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe solution was cooled
  4. temperatureAfter an additional period of two hours at reflux the mixture
  5. filtrationwas filtered
  6. customthe solvent was removed from the filtrate by flash evaporation
  7. washwashed with 5 percent aqueous hydrochloric acid and water
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent again evaporated
  10. distillationDistillation in vacuo

Sources & evidence

ORD record
ord-28168e7c94544b3ab831ef4e3fd4ca47
Source dataset
uspto-grants-1976_05
Patent number
US03956500

Reaction notes

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