Ethyl orthoformate → 3-Ethoxy-13-ethylgona-3,5-dien-17-one

HRID 1837034Notes

Reaction equation

HRID 1837034 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2].O1CCO[CH2:24][CH2:23]1.C(OCC)(OCC)OCC.C(=O)([O-])O.[Na+]>C(O)C.N1C=CC=CC=1>[CH2:23]([O:20][C:15]1[CH2:14][CH2:13][C@H:12]2[C:17](=[CH:18][CH2:19][C@H:8]3[C@H:7]4[C@@:3]([CH2:1][CH3:2])([C:4](=[O:21])[CH2:5][CH2:6]4)[CH2:11][CH2:10][C@@H:9]32)[CH:16]=1)[CH3:24]

Participants

7

Reactant 4

HCID 31214Ethyl orthoformateHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 1037926413-Ethylgon-4-ene-3,17-dione

Product 1

HCID 699137663-Ethoxy-13-ethylgona-3,5-dien-17-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

—Pyridinium-toluenesulfonate (5.0 g) was added to a solution of 13-ethylgon-4-ene-3,17-dione [Hoffmann-La Roche and Co.; AG, DE 1806410 (1967); 100.0 g] in a mixture of ethanol (600 ml), dioxane (800 ml) and triethyl orthoformate (199 ml). After 4.5 h stirring at room temperature pyridine (100 ml) was added and the reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate. The product was extracted into ethyl acetate; the combined organic phases were washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure, to give 3-ethoxy-13-ethylgona-3,5-dien-17-one (146.3 g). The product was used in the following step without further purification.

Workup

  1. additionwas added
  2. extractionThe product was extracted into ethyl acetate
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a79babb323c4f59a6e64ee4032d3a4c
Source dataset
uspto-grants-2004_08
Patent number
US06780854B2

Reaction notes

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