1: 80 percent / alkaline 2: 1.) sodium methoxide / 1.) MeOH, 0 deg C, 30 min; 2.) MeOH, reflux, 20 h 3: 99 percent / 85percent m-chloroperbenzoic acid / CH2Cl2 / 2 h 4: 72 percent / methylsulfonyl chloride, pyridine / 1.) 0 deg C, 2.) H2O, 40 deg C, 2 h 5: 98 percent / tetrahydrofuran / 5 h / Ambient temperature 6: 26 percent / 6percent sodium amalgam, disodium hydrogen phosphate / methanol / 5 h 7: 95 percent / 80percent aq. acetic acid / 0.17 h / Heating View Scheme

1: 1) NaH, 2) TFA, pyrrole / 1) N,N-dimethylacetamide, 100 deg C, 30 min., 2) CH2Cl2, room temp., 10 min. 2: 91 percent / tri-n-butyltin hydride, azobis-isobutyronitrile / dioxane / Heating View Scheme

With  sodium hydroxide in  water; acetone T=20°C; 18 h;  Show Experimental Procedure  

Multi-step reaction with 6 steps 1: 80 percent / alkaline2: 1.) sodium methoxide / 1.) MeOH, 0 deg C, 30 min; 2.) MeOH, reflux, 20 h3: 99 percent / 85percent m-chloroperbenzoic acid / CH2Cl2 / 2 h4: 72 percent / methylsulfonyl chloride, pyridine / 1.) 0 deg C, 2.) H2O, 40 deg C, 2 h5: 97 percent / tetrahydrofuran / 1 h6: 28 percent / 6percent sodium amalgam, disodium hydrogen phosphate / methanol / 5 h  

Multi-step reaction with 6 steps 1: 80 percent / alkaline2: 1.) sodium methoxide / 1.) MeOH, 0 deg C, 30 min; 2.) MeOH, reflux, 20 h3: 99 percent / 85percent m-chloroperbenzoic acid / CH2Cl2 / 2 h4: 72 percent / methylsulfonyl chloride, pyridine / 1.) 0 deg C, 2.) H2O, 40 deg C, 2 h5: 98 percent / tetrahydrofuran / 5 h / Ambient temperature6: 26 percent / 6percent sodium amalgam, disodium hydrogen phosphate / methanol / 5 h  

Multi-step reaction with 6 steps 1: 80 percent / alkaline2: 1.) sodium methoxide / 1.) MeOH, 0 deg C, 30 min; 2.) MeOH, reflux, 20 h3: 99 percent / 85percent m-chloroperbenzoic acid / CH2Cl2 / 2 h4: 72 percent / methylsulfonyl chloride, pyridine / 1.) 0 deg C, 2.) H2O, 40 deg C, 2 h5: 98 percent / tetrahydrofuran / Ambient temperature6: 28 percent / 6percent sodium amalgam, disodium hydrogen phosphate / methanol / 5 h  

Multi-step reaction with 2 steps 1: 80 percent / alkaline2: 1.) sodium methoxide / 1.) MeOH, 0 deg C, 30 min; 2.) MeOH, reflux, 20 h  

Multi-step reaction with 3 steps 1: 80 percent / alkaline2: 1.) sodium methoxide / 1.) MeOH, 0 deg C, 30 min; 2.) MeOH, reflux, 20 h3: 99 percent / 85percent m-chloroperbenzoic acid / CH2Cl2 / 2 h  

Multi-step reaction with 4 steps 1: 80 percent / alkaline2: 1.) sodium methoxide / 1.) MeOH, 0 deg C, 30 min; 2.) MeOH, reflux, 20 h3: 99 percent / 85percent m-chloroperbenzoic acid / CH2Cl2 / 2 h4: 72 percent / methylsulfonyl chloride, pyridine / 1.) 0 deg C, 2.) H2O, 40 deg C, 2 h  

Multi-step reaction with 5 steps 1: 80 percent / alkaline2: 1.) sodium methoxide / 1.) MeOH, 0 deg C, 30 min; 2.) MeOH, reflux, 20 h3: 99 percent / 85percent m-chloroperbenzoic acid / CH2Cl2 / 2 h4: 72 percent / methylsulfonyl chloride, pyridine / 1.) 0 deg C, 2.) H2O, 40 deg C, 2 h5: 98 percent / tetrahydrofuran / 5 h / Ambient temperature