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

HRID 1383023Notes

Reaction equation

HRID 1383023 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. Found: C 72.40, H 6.91, Cl 10.53; C20H23ClO2 requires: C 72.61, H 7.01, Cl 10.72. N.M.R. δp.p.m.: 0.84 (3H, s); 1.24 (3H, s); 5.13 (1H, s); 5.43 (1H, s); 6.37 (1H, d); 7.08 (1H, d). MS (m/z): 330.

Workup

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

Sources & evidence

ORD record
ord-96885470a58348d98fe221e4fdea871a
Source dataset
uspto-grants-1989_02
Patent number
US04808616

Reaction notes

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