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

chloroacetic acid in water Heating;

1: 1.) (NH4)2SO4, 1,1,1,3,3,3-hexamethyldisilazane, 2.) CsI / 1.) reflux, 15 h, 2.) MeCN, reflux, 2 h 2: 1.) lithium diisopropylamide (LDA) / 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h 3: 65 percent / 1 N aq. NaOH, 35percent H2O2 / 1 h / Ambient temperature View Scheme

1: 1.) (NH4)2SO4, 1,1,1,3,3,3-hexamethyldisilazane, 2.) CsI / 1.) reflux, 15 h, 2.) MeCN, reflux, 2 h 2: 1.) lithium diisopropylamide (LDA) / 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h View Scheme

1: 1.) (NH4)2SO4, 1,1,1,3,3,3-hexamethyldisilazane, 2.) CsI / 1.) reflux, 15 h, 2.) MeCN, reflux, 2 h 2: 1.) lithium diisopropylamide (LDA) / 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h View Scheme