Thionyl Chloride → HCID 86738085, compound

HRID 1154788Notes

Reaction equation

HRID 1154788 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

HCID 24386Thionyl ChlorideHCID 7203539HCID 7203539, compound

Product 1

HCID 86738085HCID 86738085, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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.

Workup

  1. temperatureThe solution was cooled with ice
  2. additionAfter the addition
  3. customthe mixture was reacted at room temperature for 2.5 hours
  4. stirringwith stirring
  5. concentrationThe reaction mixture was concentrated under reduced pressure, and 20 ml of anhydrous benzene
  6. additionwas added to the residue
  7. concentrationThe mixture was repeatedly concentrated under reduced pressure
  8. customto remove the thionyl chloride
  9. customThe resulting solid crude product, 3α-acetoxy-5β-cholanyl chloride, was used as a starting compound in the subsequent step without purification

Sources & evidence

ORD record
ord-9914184968be41d6bfd97753ac1df6d0
Source dataset
uspto-grants-1981_11
Patent number
US04298537

Reaction notes

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