Ammonia → HCID 68143124, compound

HRID 1414987Notes

Reaction equation

HRID 1414987 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])[CH2:2][CH2:3][CH3:4].N.[Na].[Cl-].[NH4+]>NC1C=CC=CC=1.O1CCCC1.CO.CCOCC>[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]

Participants

9

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 68144532HCID 68144532, compound

Product 1

HCID 68143124HCID 68143124, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6115AnilineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 13 -n-butyl-3-methoxygona-1,3,5(10),8-tetraen-17β-ol (0.8 g.) in aniline (20 cc.) and tetrahydrofuran (10 cc.) add liquid ammonia (100 cc.), followed by sodium (0.8 g.) in small pieces during 5 minutes while stirring the mixture. After a further 15 minutes stirring, discharge the blue color with solid ammonium chloride. Work up the product with ether in the usual way, and evaporate the resulting ether solution to leave as residue a gum; take this up in hot methanol (10 cc.), filter a little insoluble material and allow the solution to stand for 12 hours at 0° C. Crystals of 13-n-butyl-3-methoxygona-1,3,5(10)-trien-17β-ol are deposited and filtered off (0.6 g.), m.p. 123°-125° C after previous softening and a little melting at 60°-70° C.; ultraviolet absorption peak at 278 mμ (ε2,100); infrared absorption peaks at 2.86-2.97 (broad band), 6.21, 7.94, 9.62 μ.

Workup

  1. stirringAfter a further 15 minutes stirring
  2. customevaporate the resulting ether solution
  3. customto leave as residue a gum
  4. filtrationfilter a little insoluble material
  5. filtrationfiltered off (0.6 g.), m.p. 123°-125° C after previous softening
  6. customultraviolet absorption peak at 278 mμ (ε2,100)
  7. customabsorption peaks at 2.86-2.97 (broad band), 6.21, 7.94, 9.62 μ

Sources & evidence

ORD record
ord-ad2fce2d5cef42c0a39a032e118cb93c
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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