Diethyl Ether → HCID 70395379, compound

HRID 1905005Notes

Reaction equation

HRID 1905005 reaction equation
[CH2:1]1[C@@H:3]2[C:4](=[O:22])[CH:5]=[C:6]3[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][CH2:7]3.C([O:25]CC)C>C(O)(C)(C)C>[CH2:1]1[C@@H:3]2[C:4](=[O:22])[CH:5]=[C:6]3[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][C:7]3=[O:25]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 13564888HCID 13564888, compound

Product 1

HCID 70395379HCID 70395379, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 1,2β-methylenandrost-4-ene-3,17-dione (0.2 g) in tert-butanol (5 ml) potassium tert-butoxide (0.26 g) is added and the mixture stirred vigorously for 24 hours at room temperature. Then ice water and diethyl ether are added, the ethereal extract washed with water, dried, and concentrated under reduced pressure. The residue is chromatographed on silica gel using n-hexane/ethyl acetate to give 0.15 g of 1,2β-methylenandrost-4-ene-3,6,17-trione. Found: C 81.01, H 8.05. C20H24O2 requires: C 81.04, H 8.16.

Workup

  1. extractionthe ethereal extract
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-f3fbe9af16c7424bbf0cb4a7f4978c39
Source dataset
uspto-grants-1989_06
Patent number
US04840943

Reaction notes

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