4,9,15-Estratriene-3,17-dione → 15beta-n-Butyl-4,9-estradiene-3,17-dione

HRID 746158Notes

Reaction equation

HRID 746158 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Cu]C#N.[CH3:9][C@:10]12[CH2:26][CH2:25][C:24]3[C@@H:15]([CH2:16][CH2:17][C:18]4[C:23]=3[CH2:22][CH2:21][C:20](=[O:27])[CH:19]=4)[C@@H:14]1[CH:13]=[CH:12][C:11]2=[O:28]>CCCCCC.O1CCCC1.N>[CH2:1]([C@H:13]1[C@H:14]2[C@H:15]3[C:24]([CH2:25][CH2:26][C@:10]2([CH3:9])[C:11](=[O:28])[CH2:12]1)=[C:23]1[C:18](=[CH:19][C:20](=[O:27])[CH2:21][CH2:22]1)[CH2:17][CH2:16]3)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 134236124,9,15-Estratriene-3,17-dioneHCID 178418339ButyllithiumHCID 178418546HCID 178418546, compound

Product 1

HCID 1342361815beta-n-Butyl-4,9-estradiene-3,17-dione

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

6.25 ml of a 15% solution of n-butyllithium in hexane are added to a suspension of 500 mg of copper(I) cyanide in 10 ml of absolute tetrahydrofuran drop by drop at -78° C. After addition, it is stirred for 15 minutes more at -78° C., before a solution of 1.2 g of 4,9,15-estratriene-3,17-dione in 20 ml of absolute tetrahydrofuran is added drop by drop. Then it is stirred for 90 minutes, during which the temperature of the reaction solution is allowed gradually to rise to -20° C. For finishing, it is poured in concentrated aqueous ammonia solution and extracted with ethyl acetate. After recrystallization of the crude product from ethyl acetate/diisopropyl ether, 940 mg of 15β-n-butyl-4,9-estradiene-3,17-dione with a melting point of 159° to 161° C. are obtained.

Workup

  1. additionAfter addition, it
  2. additionis added drop by drop
  3. customto rise to -20° C
  4. extractionextracted with ethyl acetate
  5. customAfter recrystallization of the crude product from ethyl acetate/diisopropyl ether, 940 mg of 15β-n-butyl-4,9-estradiene-3,17-dione with a melting point of 159° to 161° C.
  6. customare obtained

Sources & evidence

ORD record
ord-fdd33dda73da44feb27ec65d92ba6a82
Source dataset
uspto-grants-1986_07
Patent number
US04603013

Reaction notes

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