Pyridine → Estradiol diacetate

HRID 1900544Notes

Reaction equation

HRID 1900544 reaction equation
[CH3:1][C@@:2]12[C@@H:18]([OH:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.N1C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].[O:34]1CC[CH2:36][CH2:35]1>>[CH3:28][C:27]([O:19][C@@H:18]1[C@@:2]2([CH3:1])[CH2:3][CH2:4][C@@H:5]3[C:6]4[CH:7]=[CH:8][C:9]([O:20][C:35]([CH3:36])=[O:34])=[CH:10][C:11]=4[CH2:12][CH2:13][C@H:14]3[C@@H:15]2[CH2:16][CH2:17]1)=[O:29]

Participants

5

Reactant 4

HCID 1049PyridineHCID 5757EstradiolHCID 7918Acetic AnhydrideHCID 8028Tetrahydrofuran

Product 1

HCID 66431Estradiol diacetate

Procedure

Estradiol (50 g), pyridine (90 g), and dry tetrahydrofuran (400 ml) were placed in a four-neck flask (1 liter). Then, acetic anhydride (94 g) was added thereto and the mixture was refluxed for 6 hours under stirring. The pyridine in the solution was concentrated to about 1/3 volume. Then, ethyl acetate (400 ml) and distilled water (300 ml) were added, and the mixture was shaken for extraction. The organic layer was washed two times with equal volumes of distilled water. The organic layer was dried over magnesium sulfate, and then dried under reduced pressure to obtain white crystals (estradiol-3,17β-diacetate; 64.1 g).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. concentrationThe pyridine in the solution was concentrated to about 1/3 volume
  3. distillationThen, ethyl acetate (400 ml) and distilled water (300 ml)
  4. additionwere added
  5. stirringthe mixture was shaken for extraction
  6. washThe organic layer was washed two times with equal volumes of distilled water
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-790e9a6e2b0b4350af08b9b7fc83bab1
Source dataset
uspto-grants-1996_11
Patent number
US05576309

Reaction notes

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