N-bromobutanimide → HCID 22841570, compound

HRID 1382730Notes

Reaction equation

HRID 1382730 reaction equation
[CH2:1]([C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH2:11][C:10](=[CH2:23])[C:9]1=[CH:8][C:7](=[O:24])[CH2:6][CH2:5]2)[C:2]#[CH:3].[Br:25]N1C(=O)CCC1=O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:25][C:3]#[C:2][CH2:1][C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH2:11][C:10](=[CH2:23])[C:9]1=[CH:8][C:7](=[O:24])[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22841568HCID 22841568, compound

Product 1

HCID 22841570HCID 22841570, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

A solution of 484 mg of 10β-(2-propynyl)-6-methylenestr-4-ene-3,17-dione in 20 ml of acetone is treated at room temperature with 312 mg of N-bromosuccinimide and 25 mg of silver nitrate, and stirred 4 hours at room temperature in the dark. The mixture is poured with stirring into ice-water and the formed precipitate is filtered off and dissolved in ethyl acetate. The resulting solution is washed with water, dried, evaporated to dryness in vacuo, and the crude is purified by flash chromatography on SiO2, eluting with n-hexane:diethylether 20:80 to give 363 mg of the title compound as a white crystalline product,

Workup

  1. additionThe mixture is poured
  2. filtrationthe formed precipitate is filtered off
  3. dissolutiondissolved in ethyl acetate
  4. washThe resulting solution is washed with water
  5. customdried
  6. customevaporated to dryness in vacuo
  7. customthe crude is purified by flash chromatography on SiO2
  8. washeluting with n-hexane:diethylether 20:80

Sources & evidence

ORD record
ord-3713a2ce9afc475a9cc9bc2efa982b43
Source dataset
uspto-grants-1989_02
Patent number
US04808578

Reaction notes

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