1: thionyl chloride / 1.) room temperature, 45 min, 2.) 45 deg C, 2 h 2: 91 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 3: 82 percent / dimethylsulfoxide / 1 h / Ambient temperature 4: 70.5 percent / zinc, acetic acid / dimethylformamide / 0.75 h / 0 °C 5: thionyl chloride / dimethylformamide / 4 h / 40 - 45 °C 6: 79 percent / pyridine / diethyl ether / 30 h / Heating 7: 1.) sodium hydride, 2.) 1,2-bis(diphenylphosphino)ethane / 2.) tetrakis(triphenylphosphine)palladium(0) / 1,) THF, 0 deg C, 30 min; room temperature, 15 min, 2.) reflux 8: 86 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 3 h / 95 - 100 °C 9: 94 percent / disodium hydrogen phosphate, 6percent sodium amalgam / ethanol; tetrahydrofuran / 0.75 h / -20 °C View Scheme

toluene-4-sulfonic acid in toluene RefluxDean-Stark;

(i) NaI, butanone, (ii) /BRN= 610776/; Multistep reaction;

triphenylphosphine in 7-bromoheptanoic acid; acetonitrile; benzene

1: (i) Ph3P, NaH, MeCN, DMSO, (ii) /BRN= 2553708/ 2: CrO3, H2SO4 / acetone 3: aq. NaOH / ethanol 4: diethyl ether View Scheme

1: LiAlH4, conc. H2SO4 / tetrahydrofuran / 0.25 h / T < 2 deg C 2: 82 percent / TsOH*H2O / CH2Cl2 / 0 °C View Scheme

(i) LiNH2, liq. NH3, THF, (ii) /BRN= 1745664/, THF; Multistep reaction;

2: NaCH2SOCH3 / dimethylsulfoxide / 0.5 h View Scheme

(i) NaI, (ii) /BRN= 773645/, H2SO4; Multistep reaction;

1: (i) Ph3P, NaH, MeCN, DMSO, (ii) /BRN= 2553708/ 2: CrO3, H2SO4 / acetone View Scheme