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

HRID 1077209Notes

Reaction equation

HRID 1077209 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]

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 222AmmoniaSolventHCID 79001-Methoxy-2-propanolSolventHCID 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 one 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 one 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-a4d73eef04a44922a060cdfff8b9bfba
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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