1-Iodopropane → HCID 22119025, compound

HRID 1275110Notes

Reaction equation

HRID 1275110 reaction equation
[Na].[C:2]1(=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:11]([OH:13])=[O:12])[CH:9]=2)[CH2:4][CH2:3]1.I[CH2:16][CH2:17][CH3:18]>CO>[CH2:16]([S:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][C:2]2=[O:14])=[CH:6][CH:7]=1)(=[O:13])=[O:12])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 5360545SodiumHCID 22119038HCID 22119038, compound

Product 1

HCID 22119025HCID 22119025, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.25 g of sodium is dissolved in 50 ml of anhydrous methanol. 1.96 g of indan-1-one-6-sulfinic acid (see above) are added in portions and the mixture is stirred for 30 min at room temp. 1.87 g of 1-iodopropane are then added and the mixture is stirred for 4 hours at reflux temp. For completion of the reaction, the mixture is concentrated in vacuo, treated with 5 ml of iodopropane and 10 ml of toluene and heated to reflux for 2 hours. It is then concentrated, the residue is extracted by shaking with water and CH2Cl2, the org. phase is dried and concentrated, and the residue is purified by column filtration (SiO2 ; cyclohexane/ethyl acetate=2/1). 6-(Propane-1-sulfonyl)indan-1-one of melting point 100° C. is obtained.

Workup

  1. stirringthe mixture is stirred for 4 hours
  2. temperatureat reflux temp
  3. customFor completion of the reaction
  4. concentrationthe mixture is concentrated in vacuo
  5. additiontreated with 5 ml of iodopropane and 10 ml of toluene
  6. temperatureheated
  7. temperatureto reflux for 2 hours
  8. concentrationIt is then concentrated
  9. extractionthe residue is extracted
  10. stirringby shaking with water and CH2Cl2
  11. customphase is dried
  12. concentrationconcentrated
  13. filtrationthe residue is purified by column filtration (SiO2 ; cyclohexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-57bf79dce3d14c6f97f53f972d11d851
Source dataset
uspto-grants-2000_12
Patent number
US06159996

Reaction notes

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