1: 99 percent / triethylamine / CH2Cl2 / 1.) 0-5 deg C, 15 min, 2.) 2 h, 0-5 deg C 2: 93 percent / dicyclohexyl-18-crown-6 ether / acetonitrile / 1.) RT, 4 h, 2.) reflux, 2 h 3: 97.7 percent / KOH / H2O; ethanol / 48 h 4: 75 percent / PPA / 2 h / 100 °C 5: NaBH4 / methanol / 16 h / Ambient temperature 6: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h 7: N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / Heating 8: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min View Scheme

1: 99 percent / triethylamine / CH2Cl2 / 1.) 0-5 deg C, 15 min, 2.) 2 h, 0-5 deg C 2: 93 percent / dicyclohexyl-18-crown-6 ether / acetonitrile / 1.) RT, 4 h, 2.) reflux, 2 h 3: 97.7 percent / KOH / H2O; ethanol / 48 h 4: 75 percent / PPA / 2 h / 100 °C 5: NaBH4 / methanol / 16 h / Ambient temperature 6: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: dicyclohexyl-18-crown-6 ether / 1.) 0-5 deg C, 2.) 12 h, RT<br />2: borane-dimethyl sulfide<br /> <br /> &nbsp;