Thionyl Chloride → 1-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chloride

HRID 73394Notes

Reaction equation

HRID 73394 reaction equation
[CH2:1]([C:4]1([S:7]([O-:10])(=O)=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[K+].S(Cl)([Cl:14])=O>CN(C=O)C>[CH2:1]([C:4]1([S:7]([Cl:14])(=[O:10])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 467801201-Allylcyclopropanesulfonic Acid Potassium Salt

Product 1

HCID 441819591-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

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).

Workup

  1. customThe volatiles evaporated under reduced pressure
  2. extractionthe residue extracted with CH2Cl2 (50 ml)
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-e4e738bec7e5404fb954877e0388aa79
Source dataset
uspto-grants-2014_09
Patent number
US08829052B2

Reaction notes

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