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Diethyl Ether → 13-Ethyl-17beta-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene

HRID 1077208
Notes
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Reaction equation

HRID 1077208 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:11]([C@:13]12[CH2:21][CH2:20][C@@H:19]3[C:22]4[CH:23]=[CH:24][C:25]([O:30][CH3:31])=[CH:26][C:27]=4[CH2:28][CH2:29][C@H:18]3[C@@H:17]1[CH2:16][CH2:15][C:14]2=[O:32])[CH3:12].[CH3:33][CH2:34][O:35]CC>S(=O)(=O)(O)O>[CH2:11]([C@:13]12[CH2:21][CH2:20][C@@H:19]3[C:22]4[CH:23]=[CH:24][C:25]([O:30][CH3:31])=[CH:26][C:27]=4[CH2:28][CH2:29][C@H:18]3[C@@H:17]1[CH2:16][CH2:15][C@@H:14]2[O:32][CH2:33][CH2:34][OH:35])[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 6451240Aluminum(III) ChlorideHCID 11087833EthylmetrienoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 6814377113-Ethyl-17beta-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene

Reagents, catalysts & solvents 1

HCID 1118
Sulfuric Acid
Solvent

Procedure

Prepare a solution of ether (100 ml), aluminum chloride (13.3 g) and lithium aluminum hydride (15 ml. of a 1 M solution). Stir for 20 minutes. Add to a cool solution of dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one, cyclic ethylene ketal (17.1 g) in ether (1,000 ml). Stir the reaction mixture and cool in an ice-water bath for 4 hours. Dilute with 2 N sulfuric acid until a clear solution results. Separate the ether layer, wash with saturated sodium bicarbonate solution, and evaporate. Treat the residue with ethanol (200 ml), concentrated hydrochloric acid (5 ml) and water (10 ml) on a steam bath for 30 minutes. Evaporate, then recrystallize from ethanol to obtain dl-13-ethyl-17β-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene (8.1 g), m.p. 131°-132°; ultraviolet absorption peak at 278 mμ (ε2,130), infrared maximum at 2.93 μ.

Workup

  1. stirringStir the reaction mixture
  2. temperaturecool in an ice-water bath for 4 hours
  3. customresults
  4. customSeparate the ether layer
  5. washwash with saturated sodium bicarbonate solution
  6. customevaporate
  7. additionTreat the residue with ethanol (200 ml), concentrated hydrochloric acid (5 ml) and water (10 ml) on a steam bath for 30 minutes
  8. customEvaporate
  9. customrecrystallize from ethanol

Sources & evidence

ORD record
ord-2aa437aa8ea74519972f6658075553ee
Source dataset
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03959322

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes