Ammonia → HCID 53821585, compound

HRID 1077175Notes

Reaction equation

HRID 1077175 reaction equation
[CH2:1]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[CH:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])[CH2:2][CH2:3][CH3:4].[Li].N.C(O)C>O1CCCC1.CCOCC.O>[CH2:1]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH2:15][CH:16]=[C:17]([O:22][CH3:23])[CH2:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 3028194LithiumHCID 68143124HCID 68143124, compound

Product 1

HCID 53821585HCID 53821585, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 13β-n-butyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (0.5 g.) in a mixture of tetrahydrofuran (5 cc.) and ether (15 cc.) dropwise to a stirred solution of lithium (0.5 g.) in liquid ammonia (60 cc.). After 5 minutes beyond completion of addition, add ethanol (8 cc.) dropwise and when the blue color is discharged, add water and extract the mixture with ether. Work up in the usual way to give 13β-n-butyl-3-methoxy-gona-2,5(10)-dien17β-ol as a crystalline solid, m.p. 135°-9°; infrared absorption peaks at 2.97, 6.25, 6.38 and 8.16 μ.

Workup

  1. additionAfter 5 minutes beyond completion of addition
  2. extractionextract the mixture with ether

Sources & evidence

ORD record
ord-c1a7ac4b7c01483c8c973aeaefd915d6
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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