Potassium Carbonate → Methanesulfonic acid (R)-5-hydroxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester
Reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:3]=1[O:4][CH2:5][C@H:6](OS(C)(=O)=O)[CH2:7][O:8][S:9]([CH3:12])(=[O:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:1][C:2]1[C:3]2[O:4][CH2:5][C@H:6]([CH2:7][O:8][S:9]([CH3:12])(=[O:10])=[O:11])[O:22][C:18]=2[CH:19]=[CH:20][CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of methanesulfonic acid (S)-3-(2,6-dihydroxy-phenoxy)-2-methanesulfonyloxy-propyl ester (253 g, 7.10 mmol) and potassium carbonate (1.14 g, 8.30 mmol) in acetone (30 ml) was refluxed under nitrogen atmosphere for 3.5 h. The reaction mixture was cooled down, filtered and evaporated to dryness. The crude product was purified with flash chromatography using dichloromethane and ethyl acetate as eluents to give 0.75 g of the title compound.