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

HRID 1154789Notes

Reaction equation

HRID 1154789 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>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

4

Reactant 2

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

Product 1

HCID 867380843beta-Acetoxychol-5-enyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3β-Acetoxychol-5-enic acid (500 g; 1.2 moles) was added to 8 liters of anhydrous benzene obtained by dehydration with a molecular sieve. The resulting solution was cooled with ice, and with stirring, 390 ml (5.4 moles) of thionyl chloride was added dropwise. After the addition, the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, and 2 liters of anhydrous benzene resulting from dehydration with a molecular sieve was added to the residue. The mixture was repeatedly concentrated under reduced pressure (five times) to remove the thionyl chloride contained in the residue. The resulting solid crude product, 3β-acetoxychol-5-enyl chloride, was used in the subsequent step as a starting compound without purification.

Workup

  1. customobtained by dehydration with a molecular sieve
  2. temperatureThe resulting solution was cooled with ice
  3. additionAfter the addition
  4. stirringthe mixture was stirred at room temperature for 4 hours
  5. concentrationThe reaction mixture was concentrated under reduced pressure, and 2 liters of anhydrous benzene resulting from dehydration with a molecular sieve
  6. additionwas added to the residue
  7. concentrationThe mixture was repeatedly concentrated under reduced pressure (five times)
  8. customto remove the thionyl chloride
  9. customThe resulting solid crude product, 3β-acetoxychol-5-enyl chloride, was used in the subsequent step as a starting compound without purification

Sources & evidence

ORD record
ord-1f63967a03ba4cec83e4b55f7f942e53
Source dataset
uspto-grants-1981_11
Patent number
US04298537

Reaction notes

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