Hydrochloric Acid → Androsta-1,4-diene-3,17-dione, 4-chloro-6-methylene-

HRID 1200170Notes

Reaction equation

HRID 1200170 reaction equation
O1[C:3]23[C@:16]([CH3:21])([CH:17]=[CH:18][C:19](=[O:20])[CH:2]12)[C@@H:15]1[C@H:6]([C@H:7]2[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C:10](=[O:22])[CH2:9][CH2:8]2)[CH2:5][C:4]3=[CH2:23].[ClH:24]>C(O)(=O)C>[Cl:24][C:2]1[C:19](=[O:20])[CH:18]=[CH:17][C@@:16]2([CH3:21])[C:3]=1[C:4](=[CH2:23])[CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15859119HCID 15859119, compound

Product 1

HCID 15859117Androsta-1,4-diene-3,17-dione, 4-chloro-6-methylene-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4,5-epoxy-6-methylenandrost-1-ene-3,17-dione (1.0 g) in glacial acetic acid (10 ml) was treated with gaseous hydrogen chloride for 30 min at room temperature The precipitate was filtered off, washed with diethyl ether, dried and chromatographed on silica gel using hexane/ethyl acetate to yield 0.8 g of pure 4-chloro-6-methylenandrosta-1,4-diene-3,17-dione.

Workup

  1. filtrationwas filtered off
  2. washwashed with diethyl ether
  3. customdried
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-2626aa062f254304a4a546a47dd63b17
Source dataset
uspto-grants-1990_02
Patent number
US04904650

Reaction notes

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