1: 86 percent / K2CO3 / dimethylformamide / 0.25 h / 80 °C 2: 92 percent / OsO4; 2-methyl-2-propanol; NaIO4 / dioxane; H2O / 2 h / 20 °C 3: 71 percent / tetra-n-butylammonium bromide; BF3-Et2O / CHCl3 / 0.5 h / Heating 4: 90 percent / Et3N; formic acid / Pd(AcO)2 / dimethylformamide / 11 h / 80 °C View Scheme

1: 51.7 percent / K2CO3, KI / acetone / 24 h / Heating 2: 74.6 percent / N,N-dimethylaniline / 12 h / Heating View Scheme