Water → HCID 69912153, compound

HRID 353702Notes

Reaction equation

HRID 353702 reaction equation
[CH2:1]([C@@H:3]1[CH2:20][C:19]2[C@H:14]([CH2:15][CH2:16][C:17](=[O:21])[CH:18]=2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:22])[CH2:7][CH2:6]1)[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].O>N1C=CC=CC=1>[C:23]([O:22][C@H:8]1[CH2:7][CH2:6][C@H:5]2[C@H:4]3[C@H:13]([CH2:12][CH2:11][C@:9]12[CH3:10])[C@@H:14]1[C:19](=[CH:18][C:17](=[O:21])[CH2:16][CH2:15]1)[CH2:20][C@H:3]3[CH2:1][CH3:2])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic Anhydride2×HCID 9882865HCID 9882865, compound

Product 1

HCID 69912153HCID 69912153, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

i)—A solution of (7α,17β)-7-ethyl-17-hydroxyestr-4-en-3-one (Example 1, 2.0 g) in dry pyridine (15 ml) was treated with acetic anhydride (1.86 ml) and the reaction mixture was stirred at room temperature for 6.5 h; additional acetic anhydride (1.86 ml) was added after 3 h. The mixture was cooled to 0° C.; water was added and stirring was continued for 30 min. 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 (7α,17β)-17-(acetyloxy)-7-ethylestr-4-en-3-one (2.15 g). The product was used in the next step without further purification.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringstirring
  3. waitwas continued for 30 min
  4. extractionThe product was extracted into ethyl acetate
  5. washthe combined organic phases were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27fb603a3f3842edb099d2b147dd33d4
Source dataset
uspto-grants-2004_06
Patent number
US06756366B1

Reaction notes

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