Water → 1,17beta-Diacetoxy-3-methoxyestra-1,3,5(10)-triene

HRID 839751Notes

Reaction equation

HRID 839751 reaction equation
[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([OH:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1)(=[O:3])[CH3:2].O.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([O:23][C:27](=[O:29])[CH3:28])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 706142631-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17beta-ol

Product 1

HCID 539516301,17beta-Diacetoxy-3-methoxyestra-1,3,5(10)-triene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-acetoxy-3-methoxyestra-1,3,5(10)-triene-17β-ol (0.95 g, 2.8 mM) in 20 ml of acetic anhydride and 5 ml of pyridine is heated on a steam bath for 1 hr. The resulting yellow solution is cooled and poured into 300 ml of cold H2O. The suspension is filtered, and the resulting white solid is recrystallized from methanol-H2O to give 1,17β-diacetoxy-3-methoxyestra-1,3,5(10)-triene as a white solid, yield 0.75 g (70%); m.p. 120°-121°.

Workup

  1. temperatureThe resulting yellow solution is cooled
  2. filtrationThe suspension is filtered
  3. customthe resulting white solid is recrystallized from methanol-H2O

Sources & evidence

ORD record
ord-801507583caa4e9bb1050334f8cecac2
Source dataset
uspto-grants-1978_06
Patent number
US04096253

Reaction notes

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