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Sodium Sulfide → 3-Acetoxy-7alpha-(5-acetoxypentyl)-16alpha-bromo-17,17-ethylenedioxy-estra-1,3,5(10)-triene

HRID 361642
Notes
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Reaction equation

HRID 361642 reaction equation
[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14]3([O:26][CH2:25][CH2:24][O:23]3)[CH2:13][CH2:12]4)[C@H:9]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33](=[O:35])[CH3:34])[CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].C1C=C[NH+]=CC=1.[Br:42][Br-]Br.[S-2].[Na+].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14]3([O:26][CH2:25][CH2:24][O:23]3)[C@H:13]([Br:42])[CH2:12]4)[C@H:9]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33](=[O:35])[CH3:34])[CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 14804Sodium SulfideHCID 15838160HCID 15838160, compound

Product 1

HCID 158381613-Acetoxy-7alpha-(5-acetoxypentyl)-16alpha-bromo-17,17-ethylenedioxy-estra-1,3,5(10)-trieneYield 100.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 63.2 g of 3-acetoxy-7α-(5-acetoxypentyl)-17,17-ethylenedioxy-estra-1,3,5(10)-triene in 630 ml of tetrahydrofuran is mixed in portions at 0° C. with 61.7 g of pyridine hydrobromide perbromide, and it is stirred for 2 hours at 0° C. Then, a solution of 15 g of sodium sulfide in 70 ml of water is added, diluted with ethyl acetate, washed with sodium bicarbonate and common salt solution and dried on sodium sulfate and concentrated by evaporation in a vacuum. 74.1 g of 3-acetoxy-7α-(5-acetoxypentyl)-16α-bromo-17,17-ethylenedioxy-estra-1,3,5(10)-triene is obtained as oil.

Workup

  1. washwashed with sodium bicarbonate and common salt solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-99ccf0ea848a43739ebcc4275b7c7031
Source dataset
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05866560

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes