Thionyl Chloride → 3beta-Acetoxychol-5-enyl chloride

HRID 1154786Notes

Reaction equation

HRID 1154786 reaction equation
[C:1]([O:4][C@H:5]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C:7](=[CH: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.[Na]>C1C=CC=CC=1>[C:1]([O:4][C@H:5]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C:7](=[CH: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

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 111017913beta-Acetoxy-5-cholenic acid

Product 1

HCID 867380843beta-Acetoxychol-5-enyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

3β-Acetoxychol-5-enic acid (4.16 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 stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and to the resulting residue was added 20 ml of anhydrous benzene which had been obtained by dehydrating benzene with sodium. The mixture was repeatedly concentrated under reduced pressure to remove the thionyl chloride contained in the residue. The resulting crude solid product, 3β-acetoxychol-5-enyl 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. stirringthe mixture was stirred at room temperature for 2.5 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionto the resulting residue was added 20 ml of anhydrous benzene which
  6. customhad been obtained
  7. concentrationThe mixture was repeatedly concentrated under reduced pressure
  8. customto remove the thionyl chloride
  9. customThe resulting crude solid product, 3β-acetoxychol-5-enyl chloride, was used as a starting compound in the subsequent step without purification

Sources & evidence

ORD record
ord-13004a65aac1405aa2171bb326a118b1
Source dataset
uspto-grants-1981_11
Patent number
US04298537

Reaction notes

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