Réaction #595322

ord-4f96d1fe87c14ca99ef2063384456be5

Équation de réaction

C=CCC1(S(=O)(=O)[O-])CC1.[K+]
potassium 1-allylcyclopropane-1-sulfonate
O=S(Cl)Cl
thionyl chloride
C=CCC1(S(=O)(=O)Cl)CC1
crude product
C=CCC1(S(=O)(=O)Cl)CC1
1-allylcyclopropane-1-sulfonyl chloride

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe volatiles evaporated under reduced pressure
  2. 2
    Extractionthe residue extracted with CH2Cl2 (50 ml)
  3. 3
    LavageThe extract was washed with water
  4. 4
    Séchagedried (MgSO4)
  5. 5
    Autreevaporated

Mode opératoire

A solution of potassium 1-allylcyclopropane-1-sulfonate (3.44 g, 17.2 mmol), thionyl chloride (10 ml) and DMF (5 drops) was refluxed at 60° C. for 16 h. The volatiles evaporated under reduced pressure and the residue extracted with CH2Cl2 (50 ml). The extract was washed with water, dried (MgSO4) and evaporated to obtain the crude product as yellow gummy oil which was washed with hexane and used in the next reaction without further purification (2.7 g, 15 mmol, 87%). 1HNMR (300 MHz, CDCl3): δ 5.728 (m, 1H), 5.191 (t, 2H), 2.9 (d, 2H), 0.756 (m, 2H), 0.322 (m, 2H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09095581B2uspto-grants-2015_08