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

HRID 1414991
Notes
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Reaction equation

HRID 1414991 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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 of 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-249c6b9f577f4c5db6a225781351a3af
Source dataset
uspto-grants-1977_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04002746

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes