Ethyl orthoformate → HCID 69913767, compound

HRID 353705Notes

Reaction equation

HRID 353705 reaction equation
[CH3:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:21])[CH2:6][CH2:5]1.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:21][C:7]1[CH2:6][CH2:5][C@H:4]2[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:3]2[C@@H:2]([CH3:1])[CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C:16]2=[O:20])[CH:8]=1)[CH3:24]

Participants

7

Reactant 4

HCID 31214Ethyl orthoformateHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 54057431HCID 54057431, compound

Product 1

HCID 69913767HCID 69913767, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

—Pyridinium p-toluenesulfonate (1.65 g) was added to a solution of (11β)-11-methylestr-4-ene-3,17-dione [van den Broek, A. J. et al, Steroids 30, 481 (1977); 16.86 g] in a mixture of ethanol (110 ml), dioxane (220 ml) and triethyl orthoformate (35.0 ml). After 4 h stirring at room temperature pyridine 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 (11β)-3-ethoxy-11-methylestra-3,5-dien-17-one (21.84 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-39ed505d1b9f4c9f9f8324476f0ef4c3
Source dataset
uspto-grants-2004_06
Patent number
US06756366B1

Reaction notes

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