Ammonia → HCID 68144627, compound

HRID 1415047Notes

Reaction equation

HRID 1415047 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 isopronanol to obtain a product with m.p. 130°-134°; ultaviolet absorption peak at 280 mμ (ε1,976), no infrared absorption in the ketone region.

Sources & evidence

ORD record
ord-1d30f67c152b431a992af6b1f2a9db08
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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