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

HRID 361642Notes

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]

Participants

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

washwashed with sodium bicarbonate and common salt solution
customdried on sodium sulfate
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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