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Water → 13-Ethyl-17beta-(2-hydroxyethoxy)-3-methoxygona-2,5(10)-diene

HRID 1415029
Notes
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Reaction equation

HRID 1415029 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[O:22][CH2:23][CH2:24][OH:25])[CH3:2].[Li].[Cl-].[NH4+].O>COCC(O)C.O1CCCC1.N>[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[O:22][CH2:23][CH2:24][OH:25])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 6814377113-Ethyl-17beta-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene

Product 1

HCID 6814401413-Ethyl-17beta-(2-hydroxyethoxy)-3-methoxygona-2,5(10)-dieneYield 84.5%

Reagents, catalysts & solvents 3

HCID 222
Ammonia
Solvent
HCID 79001-Methoxy-2-propanolSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve dl-13-ethyl-17β-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene (4.0 g) in 1-methoxy-2-propanol (60 ml), tetrahydrofuran (120 ml) and liquid ammonia (300 ml). Gradually add lithium (4.0 g) with stirring over a period of 1 hour. Add ammonium chloride (8.0 g) and water. Filter, wash and dry the resulting precipitate. Dissolve the product in tetrahydrofuran (300 ml) and liquid ammonia (300 ml) and treat with lithium (4.0 g). Stir for 1 hour. Add absolute ethanol, then water. Filter the resulting precipitate and wash it with water to obtain dl-13-ethyl-17β-(2-hydroxyethoxy)-3-methoxygona-2,5(10)-diene (3.4 g); essentially no ultraviolet absorption at the 280 mμ region, infrared absorption maxima at 2.91 μ, 5.89 μ, 6.0 μ.

Workup

  1. filtrationFilter
  2. washwash
  3. customdry the resulting precipitate
  4. dissolutionDissolve the product in tetrahydrofuran (300 ml)
  5. additionliquid ammonia (300 ml) and treat with lithium (4.0 g)
  6. additionAdd absolute ethanol
  7. filtrationFilter the resulting precipitate
  8. washwash it with water

Sources & evidence

ORD record
ord-293d70b8162c4d12b2855e66d7d789bd
Source dataset
uspto-grants-1977_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04002746

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes