Ammonia → HCID 68143735, compound

HRID 1077241Notes

Reaction equation

HRID 1077241 reaction equation
[CH2:1]([C@:3]1([OH:23])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:4]12[CH3:5])[C:17]1[CH:16]=[CH:15][C:14]([O:21][CH3:22])=[CH:13][C:12]=1[CH2:11][CH2:10]3)[CH3:2].N.[Li].[Cl-].[NH4+]>CCOCC.O.C(O)C>[CH2:1]([C@:3]1([OH:23])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:4]12[CH3:5])[C:17]1[CH2:16][CH:15]=[C:14]([O:21][CH3:22])[CH2:13][C:12]=1[CH2:11][CH2:10]3)[CH3:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 25239917alpha-Ethylestradiol 3-methyl etherHCID 3028194Lithium

Product 1

HCID 68143735HCID 68143735, compoundYield 69.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Add dl-17α-ethyl-3-methoxyestra-1,3,5(10)-trien-17-ol (2 g) in ether (55 ml) to distlled liquid ammonia (180 ml), and add lithium (1 g) to the stirred solution. After 45 minutes add ethanol (15 ml) and ether (15 ml) dropwise followed by ammonium chloride and water. Extract with ether, wash, dry, evaporate, and recrystallize the residue from ether to obtain dl-17α-ethyl-3-methoxyestra-2,5(10)-dien-17-ol (1.4 g), m.p. 131°-134°.

Workup

  1. extractionExtract with ether
  2. washwash
  3. customdry
  4. customevaporate
  5. customrecrystallize the residue from ether

Sources & evidence

ORD record
ord-f10ffe6b6bb649ae9ec0fde34bbb87c4
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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