Thionyl Chloride → 3beta-Acetoxy-17beta-methyl-5beta-androst-14-ene

HRID 618868Notes

Reaction equation

HRID 618868 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3(O)[CH2:12][CH2:13][C@@H:14]2[CH3:24])[CH2:6]1)(=[O:3])[CH3:2].S(Cl)(Cl)=O>N1C=CC=CC=1.Cl>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C:11]3=[CH:12][CH2:13][C@@H:14]2[CH3:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 111108583beta-Acetoxy-14beta-hydroxy-17beta-methyl-5beta-androstane

Product 1

HCID 110457863beta-Acetoxy-17beta-methyl-5beta-androst-14-eneYield 94.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

To a solution of 5.0 g of 3β-acetoxy-14β-hydroxy-17β-methyl-5β-androstane (VIII-a) in pyridine (100 mL), 3.5 g of thionyl chloride were added at 0° C. The solution was stirred at the same temperature for 2.5 hrs and then poured in 100 mL of 1N HCl and crushed ice: the mixture was extracted with ethyl ether: the organic layer was washed with a saturated aqueous solution of disodium hydrogen phosphate, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to give 4.5 g of 3β-acetoxy-17β-methyl-5β-androst-14-ene as a white solid.

Workup

  1. customcrushed ice
  2. extractionthe mixture was extracted with ethyl ether
  3. washthe organic layer was washed with a saturated aqueous solution of disodium hydrogen phosphate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8928c5874f21478b988f695bc5eecb89
Source dataset
uspto-grants-1999_09
Patent number
US05955632

Reaction notes

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