sodium methylate in methanol 18 h; Ambient temperature;

1: CHCl3 / Ambient temperature 2: 58 percent / MeONa / methanol View Scheme

1: HMDS / Heating 2: CHCl3 / Ambient temperature 3: 58 percent / MeONa / methanol View Scheme

1: 94 percent / chloroacetic acid / H2O / Heating 2: HMDS / Heating 3: CHCl3 / Ambient temperature 4: 58 percent / MeONa / methanol View Scheme

1: 1.) LDA / 1.) Et2O, hexane, -78 deg C, 6 h; -12 deg C, overnight, 2.) MeOH, reflux, 6 h 2: 94 percent / chloroacetic acid / H2O / Heating 3: HMDS / Heating 4: CHCl3 / Ambient temperature 5: 58 percent / MeONa / methanol View Scheme

1: 2.1 g / stannic chloride / acetonitrile / 18 h / 0 - 4 °C 2: 85 percent / CH3ONa / methanol / 18 h / Ambient temperature View Scheme