sodium hydroxide in ethanol 1.5 h; Heating;

1: 94 percent / diethyl ether / 12 h / 0 °C 2: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 3: 90 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 2: 90 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 1.) 1.6 M BuLi / 1.) THF, hexane, 10 deg C, HMPT, 1 h; 2.) THF, 20-25 deg C 2: hydrogen / PtO2 / ethyl acetate / 15 h 3: 94 percent / tributylamine / 2 h / Heating 4: 91 percent / 10 N NaOH / Heating 6: 1.) Tl(CF3COO)3; 2.) potassium iodide / 1.) trifluoroacetic acid, 5 d, r.t.; 2.) water, 15 min 7: 81 percent / 2 N NaOH / 2 h / Heating View Scheme

1: hydrogen / PtO2 / ethyl acetate / 15 h 2: 94 percent / tributylamine / 2 h / Heating 3: 91 percent / 10 N NaOH / Heating 5: 1.) Tl(CF3COO)3; 2.) potassium iodide / 1.) trifluoroacetic acid, 5 d, r.t.; 2.) water, 15 min 6: 81 percent / 2 N NaOH / 2 h / Heating View Scheme

1: 1.) 1.6 M BuLi / 1.) THF, hexane, 10 deg C, HMPT, 1 h; 2.) THF, 20-25 deg C 2: hydrogen / PtO2 / ethyl acetate / 15 h 3: 94 percent / tributylamine / 2 h / Heating 4: 91 percent / 10 N NaOH / Heating 6: 1.) Tl(CF3COO)3; 2.) potassium iodide / 1.) trifluoroacetic acid, 5 d, r.t.; 2.) water, 15 min 7: 81 percent / 2 N NaOH / 2 h / Heating View Scheme

1: 94 percent / tributylamine / 2 h / Heating 2: 91 percent / 10 N NaOH / Heating 4: 1.) Tl(CF3COO)3; 2.) potassium iodide / 1.) trifluoroacetic acid, 5 d, r.t.; 2.) water, 15 min 5: 81 percent / 2 N NaOH / 2 h / Heating View Scheme

1: 91 percent / 10 N NaOH / Heating 3: 1.) Tl(CF3COO)3; 2.) potassium iodide / 1.) trifluoroacetic acid, 5 d, r.t.; 2.) water, 15 min 4: 81 percent / 2 N NaOH / 2 h / Heating View Scheme