Acetic Anhydride → 3-Acetoxy-7alpha-(5-acetoxypentyl)-estra-1,3,5(10)-trien-17-one

HRID 361640Notes

Reaction equation

HRID 361640 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([OH:28])[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C@H:12]1[C@@:16]([CH2:18][CH2:19]2)([CH3:17])[C:15](=[O:29])[CH2:14][CH2:13]1)(=[O:3])[CH3:2].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([O:28][C:24]1[CH:23]=[CH:22][C:21]2[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:29])[CH2:14][CH2:13]4)[C@H:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:27][C:26]=2[CH:25]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 158381587alpha-(5-Acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one

Product 1

HCID 158381593-Acetoxy-7alpha-(5-acetoxypentyl)-estra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 60.4 g of 7α-(5-acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one in 300 ml of pyridine is stirred with 150 ml of acetic anhydride for 1 hour at room temperature. Then, it is precipitated with a mixture of ice/water/common salt/hydrochloric acid, taken up with ethyl acetate, washed neutral with sodium bicarbonate and common salt solution, and dried on sodium sulfate and concentrated by evaporation in a vacuum. 63.9 g of 3-acetoxy-7α-(5-acetoxypentyl)-estra-1,3,5(10)-trien-17-one is obtained as oil.

Workup

  1. customThen, it is precipitated with a mixture of ice/water/common salt/hydrochloric acid
  2. washwashed neutral with sodium bicarbonate and common salt solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-212f200cc3564780b266b16c7fc4061d
Source dataset
uspto-grants-1999_02
Patent number
US05866560

Reaction notes

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