17alpha-Ethylestradiol 3-methyl ether → HCID 68143735, compound

HRID 1415061Notes

Reaction equation

HRID 1415061 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]>CCOCC>[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

3

Reactant 1

HCID 25239917alpha-Ethylestradiol 3-methyl ether

Product 1

HCID 68143735HCID 68143735, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add dl-17α-ethyl-3-methoxyestra-1,3,5(10)-trien-17-ol (2 g) in ether (55 ml) to distilled 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. distillationto distilled liquid ammonia (180 ml)
  2. additionadd lithium (1 g) to the stirred solution
  3. additionAfter 45 minutes add ethanol (15 ml) and ether (15 ml)
  4. extractionExtract with ether
  5. washwash
  6. customdry
  7. customevaporate
  8. customrecrystallize the residue from ether

Sources & evidence

ORD record
ord-362a3f36e34849a7a41c7912e32d9823
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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