Ammonia → (17Beta)-13-Ethyl-3-methoxygona-2,5(10)-dien-17-ol

HRID 1077173

Reaction equation

HRID 1077173 reaction equation
[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].N.[Li].[Cl-].[NH4+]>COCC(O)C.O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20][CH3:21])[CH2:16][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 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-olHCID 3028194Lithium

Product 1

HCID 101950(17Beta)-13-Ethyl-3-methoxygona-2,5(10)-dien-17-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 79001-Methoxy-2-propanolSolvent

Procedure

To 13β-ethyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (1.0 g.) in 1-methoxypropan-2-ol (100 cc.) add liquid ammonia (200 cc.), followed by lithium metal (1.2 g.) in small pieces with stirring. After discharge of the blue color add an excess ammonium chloride, followed by water; filter off the crude 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17β-ol and dry, m.p. 98°-104°. No selective ultra-violet absorption beyond 220 mμ; infrared absorption peaks at 3.03, 5.92, 6.01 μ.

Workup

  1. filtrationfilter off the crude 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17β-ol
  2. customdry
  3. customNo selective ultra-violet absorption beyond 220 mμ
  4. custominfrared absorption peaks at 3.03, 5.92, 6.01 μ

Sources & evidence

ORD record
ord-e3143b7af7464c89a6c753fe74b87862
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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