Thionyl Chloride → HCID 86738085, compound
Reaction equation
[C:1]([O:4][C@@H:5]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:21])[CH2:16][CH2:17][C:18](O)=O)[CH2:6]1)(=[O:3])[CH3:2].S(Cl)([Cl:33])=O>C1C=CC=CC=1>[C:1]([O:4][C@@H:5]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:21])[CH2:16][CH2:17][CH2:18][Cl:33])[CH2:6]1)(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3α-Acetoxy-5β-cholanic acid (4.18 g; 10 mmoles) was added to 60 ml of anhydrous benzene. The solution was cooled with ice, and with stirring, 4.5 ml of thionyl chloride was gradually added dropwise. After the addition, the mixture was reacted at room temperature for 2.5 hours with stirring. The reaction mixture was concentrated under reduced pressure, and 20 ml of anhydrous benzene was added to the residue. The mixture was repeatedly concentrated under reduced pressure to remove the thionyl chloride contained in the residue. The resulting solid crude product, 3α-acetoxy-5β-cholanyl chloride, was used as a starting compound in the subsequent step without purification.