solid acid of tin(IV) ion-exchanged montmorillonite in dichloromethane T=0°C; Mukaiyama Aldol Addition; 0.75 h; Inert atmosphere; Reagent/catalystTemperature;

Dess-Martin periodane in dichloromethane T=0°C; 3 h; Inert atmosphere;

[2,2']bipyridinyl; copper(l) iodide; sodium t-butanolate in N,N-dimethyl-formamide T=70°C; Aldol Addition; 12 h; Inert atmosphere; Reagent/catalyst;

1: C6H5NCO, N(Et)3 / benzene View Scheme

1: C6H5NCO, N(Et)3 / benzene View Scheme

1.1: indium / tetrahydrofuran; water / 16 h / 20 °C / |Inert atmosphere 1.2: 20 °C / |Inert atmosphere 2.1: Dess-Martin periodane / dichloromethane / 3 h / 0 °C / |Inert atmosphere View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / |Inert atmosphere 1.2: 16 h / 0 - 20 °C / |Inert atmosphere 2.1: N-bromosuccinmide; toluene-4-sulfonic acid / tetrahydrofuran / 4 h / 100 °C / |Inert atmosphere 3.1: indium / tetrahydrofuran; water / 16 h / 20 °C / |Inert atmosphere 3.2: 20 °C / |Inert atmosphere 4.1: Dess-Martin periodane / dichloromethane / 3 h / 0 °C / |Inert atmosphere View Scheme

hydrogenchloride in benzene T=20°C; 4 h; various methyl aryl ketones; Product distributionMechanism;

1) THF, hexane, -78 deg C, 2 h, 2) 0 deg C, 3) DMF, room temperature, 42 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;