sodium amalgam; acetic acid

2: aqueous acetic acid; sodium-amalgam View Scheme

1: 1.) LDA / 1.) hexane, THF, -50 deg C, 30 min, 2.) hexamethylphosphoramide, -78 deg C, 1 h and room temperature, 4 h 2: 75 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 30 min, 2.) room temperature, overnight View Scheme

1: 96 percent / diethyl ether / 0.5 h / Ambient temperature 2: 1.) LDA / 1.) hexane, THF, -50 deg C, 30 min, 2.) hexamethylphosphoramide, -78 deg C, 1 h and room temperature, 4 h 3: 75 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 30 min, 2.) room temperature, overnight View Scheme

chloroform

(i) NaH, benzene, (ii) /BRN= 1912198/; Multistep reaction;

sodium in benzene Heating;