Estradiol → beta-Estradiol diacetate

HRID 1357473Notes

Reaction equation

HRID 1357473 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C@@:9]12[C@@H:25]([OH:26])[CH2:24][CH2:23][C@H:22]1[C@H:21]1[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([OH:27])=[CH:17][C:18]=3[CH2:19][CH2:20]1)[CH2:11][CH2:10]2.[CH3:28][C:29](C)=[O:30].C(Cl)Cl>N1C=CC=CC=1>[CH3:2][C:1]([O:26][CH:25]1[C:9]2([CH3:8])[CH2:10][CH2:11][CH:12]3[C:13]4[CH:14]=[CH:15][C:16]([O:27][C:29]([CH3:28])=[O:30])=[CH:17][C:18]=4[CH2:19][CH2:20][CH:21]3[CH:22]2[CH2:23][CH2:24]1)=[O:3]

Participants

5

Reactant 3

HCID 5757EstradiolHCID 7918Acetic AnhydrideHCID 21584124Propan-2-one--dichloromethane (1/1)

Product 1

HCID 3264beta-Estradiol diacetateYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under nitrogen, acetic anhydride (50 mL, 264.5 mmol) was added to a solution of estradiol (1a) (20.0 g, 73.43 mmol) in dry pyridine (200 mL). The reaction mixture was stirred at room temperature overnight (16 h). The next morning, analysis by tlc (5% acetone/CH2Cl2) indicated a complete reaction. The mixture was cooled in an ice bath and the excess acetic anhydride quenched by addition of methanol (25 mL). The mixture was stirred at 0° C. for one hour and then allowed to warm to room temperature. The solvents were removed in vacuo and the solid residue crystallized from hot methanol to give the pure diacetate (2a) (24.87 g, 95%).

Workup

  1. customa complete reaction
  2. temperatureThe mixture was cooled in an ice bath
  3. customthe excess acetic anhydride quenched by addition of methanol (25 mL)
  4. stirringThe mixture was stirred at 0° C. for one hour
  5. temperatureto warm to room temperature
  6. customThe solvents were removed in vacuo
  7. customthe solid residue crystallized from hot methanol

Sources & evidence

ORD record
ord-52a277e776e947bc82b54159aa408f4e
Source dataset
uspto-grants-2003_07
Patent number
US06593321B2

Reaction notes

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