potassium dichromate; sulfuric acid in acetone

1: 61 percent / sulfuryl chloride / CCl4 / 12 h / Ambient temperature 2: 91 percent / LiBr, Li2Co3 / dimethylformamide / 24 h / 100 °C 3: 93 percent / DIBAL-H / benzene; toluene / 2 h / 5 °C 4: 1.) BH3*THF, 2.) 3 M NaOH, 30 percent H2O2 / 1.) THF, 24 h, room temp. 2.) THF, water 5: 85 percent / K2Cr2O7-H2SO4 / acetone View Scheme

1: 1.) BH3*THF, 2.) 3 M NaOH, 30 percent H2O2 / 1.) THF, 24 h, room temp. 2.) THF, water 2: 85 percent / K2Cr2O7-H2SO4 / acetone View Scheme

1: 93 percent / DIBAL-H / benzene; toluene / 2 h / 5 °C 2: 1.) BH3*THF, 2.) 3 M NaOH, 30 percent H2O2 / 1.) THF, 24 h, room temp. 2.) THF, water 3: 85 percent / K2Cr2O7-H2SO4 / acetone View Scheme

1: 91 percent / LiBr, Li2Co3 / dimethylformamide / 24 h / 100 °C 2: 93 percent / DIBAL-H / benzene; toluene / 2 h / 5 °C 3: 1.) BH3*THF, 2.) 3 M NaOH, 30 percent H2O2 / 1.) THF, 24 h, room temp. 2.) THF, water 4: 85 percent / K2Cr2O7-H2SO4 / acetone View Scheme

sodium hydride

2: (i) MeI, (ii) /BRN= 4725512/ 3: (i) (hydrolysis), (ii) (decarboxylation) 4: NaH View Scheme

1: (i) MeI, (ii) /BRN= 4725512/ 2: (i) (hydrolysis), (ii) (decarboxylation) 3: NaH View Scheme