1: 83 percent / thionyl chloride / toluene / 12 h / 25 °C 2: 97 percent / 1.) 3M-NaOCl, t-Bu4N(+)HSO4(-), 2.) 5percent aq. KOH / multistep.: 1.) ethyl acetate-water, 20 deg C, 12 h; 2.) MeOH-water, 20 deg C, 12 h; transformation of oxazoline derivatives into carboxylic functions View Scheme

1: 83 percent / thionyl chloride / toluene / 12 h / 25 °C 2: 90 percent / 1.) n-BuLi, / diethyl ether / 1.) -78 deg C, 15 min, 0 deg C, 30 min 3: 92 percent / 1.) t-Bu4N(+)HSO4(-), 3M sodium hypochlorite, 2.) 5percent aq. KOH / 1.) ethyl acetate, water, 20 deg C, 12 h, 2.) water, MeOH, 20 deg C, 12 h View Scheme

1: 83 percent / thionyl chloride / toluene / 12 h / 25 °C 2: 90 percent / 1.) n-BuLi / hexane; diethyl ether / 1.)-78 deg C, 15 min, 0 deg C, 30 min; 2.) 20 deg C, 12 h 3: 89 percent / 1.) t-Bu4N(+)HSO4(-), 3M sodium hypochlorite, 2.) aq. KOH / 1.) ethyl acetate, water, 20 deg C, 12 h, 2.) water, MeOH, 20 deg C, 12 h View Scheme

1: 83 percent / thionyl chloride / toluene / 12 h / 25 °C 2: 78 percent / 1.) nBuLi / 1.) hexane, -78 deg C, 2.) hexane, 20 deg C, 24 h 3: 88 percent / t-BU4(+)HSO4(-), 3M sodium hypochlorite / ethyl acetate / 12 h / 20 °C View Scheme

1: SOCl2 / toluene / 16 h / 20 °C 2: 87 percent / 10 h / Heating View Scheme

thionyl chloride in toluene T=25°C; 12 h;

1: 82 percent / SOCl2 2: 1) 1.6 N BuLi / 1) ether, hexane, -78 deg C, 15 min, 2) ether 3: 98 percent / Cu-powder / acetonitrile / 50 h / Heating 4: 94 percent / NaOH / methanol; H2O / 16 h, RT; 45 min, reflux 5: 67 percent / 4 h / 0.03 Torr / Heating View Scheme