Methanol → Estradiol diacetate

HRID 2088521Notes

Reaction equation

HRID 2088521 reaction equation
[CH3:1][C:2]([O:4][C:5]([CH3:7])=[O:6])=O.[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(O)=C[C:18]=3[CH2:19][CH2:20]1)[CH2:11][CH2:10]2.C[OH:29].N1[CH:35]=[CH:34]C=CC=1>>[C:5]([O:4][C:2]1[CH:15]=[CH:14][C:13]2[C@@H:12]3[C@H:21]([C@H:22]4[C@@:9]([CH2:10][CH2:11]3)([CH3:8])[C@@H:25]([O:26][C:34](=[O:29])[CH3:35])[CH2:24][CH2:23]4)[CH2:20][CH2:19][C:18]=2[CH:1]=1)(=[O:6])[CH3:7]

Participants

5

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 5757EstradiolHCID 7918Acetic Anhydride

Product 1

HCID 66431Estradiol diacetate

Procedure

Under an N2-atmosphere, Ac2O (375 ml, 3.993 mol) was added dropwise during 20 min to a solution of estradiol (150 g, 0.551 mol) in pyridine (1500 ml). The clear colorless solution obtained was stirred at RT overnight. The reaction mixture was then cooled to 0° C. and MeOH (375 ml) was added dropwise during 25 min. The reaction mixture was stirred at 0° C. for 2 h, then allowed to warm to RT and concentrated in vacuo. The residue was recrystallized from hot MeOH to yield (C2-2) (176 g, 90%) as white crystals.

Workup

  1. customThe clear colorless solution obtained
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. stirringThe reaction mixture was stirred at 0° C. for 2 h
  4. temperatureto warm to RT
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from hot MeOH
  7. customto yield (C2-2) (176 g, 90%) as white crystals

Sources & evidence

ORD record
ord-73f48a7703e84c67b703c9239c3cc8a5
Source dataset
uspto-grants-2013_05
Patent number
US08435973B2

Reaction notes

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