Toluene → Oxolan-3-ylmethanesulfonyl chloride
Reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][S:7]([O-:10])(=O)=[O:8])[CH2:2]1.[Na+].C1(C)C=CC=CC=1.S(Cl)([Cl:21])=O>CN(C)C=O>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][S:7]([Cl:21])(=[O:10])=[O:8])[CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium tetrahydrofuran-3-ylmethanesulfonate (1.0 g) [see Preparation 10] was dissolved in dimethylformamide (0.05m)) and thionyl chloride (5.3 ml) was added. The reaction mixture was heated under reflux for 5 hours, cooled and toluene (10 ml) added. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water, the organic layer was separated, washed with brine, dried over magnesium sulphate and the solvent removed under reduced pressure to afford tetrahydrofuran-3-ylmethanesulfonyl chloride (0.22 g) as a yellow oil. 1H-NMR (CDCl3) δ: 3.95 (1H, m), 3.90-3.60 (2H, m), 3.45 (1H, m), 3.00 (2H, m), 2.30 (1H, m), 2.10 (1H, m), 1.80 (1H, m).