Ammonia → (17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol

HRID 1414989Notes

Reaction equation

HRID 1414989 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[CH:16][C:17]=4[CH2:18][CH2:19][C:8]=3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].N.[Li].[Cl-].[NH4+]>NC1C=CC=CC=1.O1CCCC1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[CH:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 11130013-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-olHCID 3028194Lithium

Product 1

HCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-olYield 82.8%

Reagents, catalysts & solvents 2

HCID 6115AnilineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 13β-ethyl-3-methoxy-gona-1,3,5(10), 8-tetraen-17β-ol (16.8 g.) dissolved in a mixture of aniline (150 cc.) and tetrahydrofuran (50 cc.) add liquid ammonia (400 cc.). Add lithium metal (6.0 g.) gradually in small pieces during 10 minutes, and stir the blue suspension obtained. After 2 hours, add ammonium chloride (50 g.) to the reaction mixture until a clear solution is obtained; then add water (600 cc.) and ether-extract the mixture. Evaporate the washed and dried extracts to obtain as residue a crystalline solid. Recrystallize from hexane (300 cc.), to obtain 13β-ethyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (14 g.), m.p. 126°-30°.

Workup

  1. customobtained
  2. customis obtained
  3. extractionthen add water (600 cc.) and ether-extract the mixture
  4. customEvaporate the
  5. washwashed
  6. customdried extracts
  7. customto obtain as residue a crystalline solid
  8. customRecrystallize from hexane (300 cc.)

Sources & evidence

ORD record
ord-de588a2c72874406a9a3784526868512
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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