Ammonia → HCID 68143913, compound

HRID 1414988Notes

Reaction equation

HRID 1414988 reaction equation
[CH2:1]([C@:5]12[CH2:13][CH2:12][C: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:10]=3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])[CH:2]([CH3:4])[CH3:3].N.NC1C=CC=CC=1.[Li].[Cl-].[NH4+]>O1CCCC1.O>[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])[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 6115AnilineHCID 25517Ammonium ChlorideHCID 3028194Lithium2×HCID 22790405HCID 22790405, compound

Product 1

HCID 68143913HCID 68143913, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add a solution of 13β-isobutyl-3-methoxygona-1,3,5(10),8-tetraen-17β-ol (17.0 g.) in dry tetrahydrofuran (125 cc.; distilled) slowly to a mixture of liquid ammonia (680 cc., distilled), aniline (85 cc., distilled) and tetrahydrofuran (125 cc.) with stirring. Then add lithium (7.9 g.) in small portions. After the addition of lithium is completed, stir the blue mixture for another 3 hours. Discharge the blue color by the cautious addition of ammonium chloride followed by warm (50°) water. Extract the crude product with benzene. Wash the extracts with water, hydrochloric acid, (20%) sodium bicarbonate, water and dry. Evaporate the solvent in vacuo to obtain a gum which on crystallization from ether-petroleum ether gives 13β-isobutyl-3-methoxygona-1,3,5(10)-trien-17β-ol (13.0 g.; 76%); m.p. 103°-104° C.: ultraviolet absorption peak at 2.78 mμ (ε 1,975); infrared absorption peak at 2.83 μ.

Workup

  1. stirringstir the blue mixture for another 3 hours
  2. extractionExtract the crude product with benzene
  3. washWash the extracts with water, hydrochloric acid, (20%) sodium bicarbonate, water
  4. customdry
  5. customEvaporate the solvent in vacuo
  6. customto obtain a gum which
  7. customon crystallization from ether-petroleum ether

Sources & evidence

ORD record
ord-9c3ca1dd520c4288876770c8cc96ce4d
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

Loading…