Ammonia → (17Beta)-13-Ethyl-3-methoxygona-2,5(10)-dien-17-ol

HRID 1414990Notes

Reaction equation

HRID 1414990 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[CH:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].N.[Li].C(O)C>O1CCCC1.CCOCC.O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20][CH3:21])[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-olHCID 3028194Lithium

Product 1

HCID 101950(17Beta)-13-Ethyl-3-methoxygona-2,5(10)-dien-17-ol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 13β-Ethyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (0.5 g.) in tetrahydrofuran (50 cc.) to stirred liquid ammonia (150 cc.), followed by lithium foil (0.5 g.) and then add ethanol (6 cc.) during 20 minutes. When the blue color is discharged, add water and work up the product with ether, to yield 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17β-ol as a solid (0.47 g.).

Sources & evidence

ORD record
ord-117baf373e194c7e8b8a1f369b9a24c1
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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