Ammonia → HCID 68144627, compound

HRID 1077227Notes

Reaction equation

HRID 1077227 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[CH:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C:8]=3[C@@H:7]1[CH2:6][CH2:5][C:4]12[O:26][CH2:25][CH2:24][O:23]1)[CH3:2].N.NC1C=CC=CC=1.[Li]>O1CCCC1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[CH:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]12[O:23][CH2:24][CH2:25][O:26]1)[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6115AnilineHCID 3028194LithiumHCID 6814418413-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8-tetraene

Product 1

HCID 68144627HCID 68144627, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add dl-13-ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8-tetraene (11.0 g) in tetrahydrofuran (160 ml) to liquid ammonia (600 ml) containing tetrahydrofuran (170 ml) and aniline (30 ml). Then add lithium (0.6 g) in small portions and stir for 2 hours. Work up in the usual way to obtain dl-13-ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10)-triene as a gum (9.5 g) that will crystallize on scratching. Recrystallize from isopropanol to obtain a product with m.p. 130°-134°; ultraviolet absorption peak at 280 mμ (ε1,976), no infrared absorption in the ketone region.

Sources & evidence

ORD record
ord-c207808103bd47e9afa8c9cb4c660c11
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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