HCID 71494339, compound → HCID 71494338, compound

HRID 508597Notes

Reaction equation

HRID 508597 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([S:13]([O-:16])(=[O:15])=[O:14])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+]>O=S(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][CH2:9][C:10]1([S:13]([O:16][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:15])=[O:14])[CH2:11][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 71494339HCID 71494339, compound

Product 1

HCID 71494338HCID 71494338, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of potassium 1-(benzyloxymethyl)cyclopropanesulfonate in SOCl2 (35 mL) and DMF (3.5 mL) was refluxed for 1.5 h and excess SOCl2 was removed under reduced pressure. Water was added carefully to the resulting mixture and extracted with ethyl acetate. The combined extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5-10% ethyl acetate/hexanes) to obtain 1-(benzyloxymethyl)cyclopropanesulfonyl chloride 2 in 97% yields (3.3 g).

Workup

  1. temperaturewas refluxed for 1.5 h
  2. customexcess SOCl2 was removed under reduced pressure
  3. additionWater was added carefully to the resulting mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (5-10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2ba40e21720d44028904253f5ce9a147
Source dataset
uspto-grants-2015_08
Patent number
US09096541B2

Reaction notes

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