Dichloromethane → 3,4-Diphenyl-3-cyclopentene-1-sulfonyl chloride
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]=1Participants
6
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.