1: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 25 deg C, 1 h 2: 51 percent / benzene; methanol / 16 h / Heating 3: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 4: hydrochloric acid / methanol View Scheme

1: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 25 deg C, 1 h 2: 51 percent / benzene; methanol / 16 h / Heating 3: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr View Scheme