Dichloromethane → 3,4-Diphenyl-3-cyclopentene-1-sulfonyl chloride

HRID 2416408Notes

Reaction equation

HRID 2416408 reaction equation
[C:1]1([C:7]2[CH2:8][CH:9](O)[CH2:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[S:20]([O:23]Cl)(=O)=[O:21].C(OCC)(=O)C.CCCCCC.C(Cl)[Cl:38]>>[C:1]1([C:7]2[CH2:8][CH:9]([S:20]([Cl:38])(=[O:23])=[O:21])[CH2:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8058HexaneHCID 8857Ethyl AcetateHCID 5091833,4-Diphenylcyclopent-3-en-1-olHCID 12750509MeSO3Cl

Product 1

HCID 223232413,4-Diphenyl-3-cyclopentene-1-sulfonyl chloride

Procedure

3,4-Diphenyl-3-cyclopenten-1-ol (5.91 g) was dissolved in the mixture of 70 mL of methylene chloride and 50 mL of pyrridine. To this reaction mixture was added 4 mL of CH3SO3Cl. After stirring overnight and reaction mixture was washed with 1 M of HCl, H2O and NaHCO3. Solution was dried over Mg2SO4 and then filtered. Solvent removal gave brown solid. About 8 mL of ethyl acetate was added followed by 150 mL of hexane producing off-white crystalline solid). After stirring overnight solid was collected on the frit, washed with 10 mL of hexane and then dried under reduced pressure to give 4.0 g of product.

Workup

  1. customreaction mixture
  2. washwas washed with 1 M of HCl, H2O and NaHCO3
  3. dry with materialSolution was dried over Mg2SO4
  4. filtrationfiltered
  5. customSolvent removal
  6. customgave brown solid
  7. stirringAfter stirring overnight solid
  8. customwas collected on the frit
  9. washwashed with 10 mL of hexane
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-7e606bffcf00474ba9a868beceb82127
Source dataset
uspto-grants-2004_11
Patent number
US06825147B2

Reaction notes

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