toluene-4-sulfonic acid in methanol 4 h;

1: 88 percent / p-Tosic acid / acetic anhydride / 14 h / Heating 2: 80 percent / DDQ / 4 h / Heating 3: 84 percent / p-Tosic Acid / methanol / 4 h View Scheme

1: 80 percent / DDQ / 4 h / Heating 2: 84 percent / p-Tosic Acid / methanol / 4 h View Scheme

1: 92 percent / N-bromoacetamide / acetic acid / 1.5 h / Ambient temperature 2: 84 percent / N-bromoacetamide, α,α-azoisobutyronitrile / CCl4 / 0.75 h / Heating 3: 1) NaOMe, 2) TFA / 1) 0 deg C, 2 h then 4 deg C, overnight, 2) CDCl3 View Scheme

1: 84 percent / N-bromoacetamide, α,α-azoisobutyronitrile / CCl4 / 0.75 h / Heating 2: 1) NaOMe, 2) TFA / 1) 0 deg C, 2 h then 4 deg C, overnight, 2) CDCl3 View Scheme

sodium methylate; trifluoroacetic acid 1) 0 deg C, 2 h then 4 deg C, overnight, 2) CDCl3; Yield given. Multistep reaction;