Water → 11beta-Fluor-7alpha-(5-iodopentyl)-estra-1,3,5(10)-triene-3,17beta-diol

HRID 1837265Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C@@H:12]([OH:27])[CH2:11][CH2:10]1.[I-:28].[Na+].O>C(C(C)=O)C>[F:26][C@H:16]1[CH2:15][C@@:13]2([CH3:14])[C@@H:9]([CH2:10][CH2:11][C@@H:12]2[OH:27])[C@H:8]2[C@H:17]1[C:18]1[CH:19]=[CH:20][C:21]([OH:25])=[CH:22][C:23]=1[CH2:24][C@H:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][I:28]

Participants

Conditions

Temperature: 90 °C

Procedure

4.29 g of 7α-(5-chloropentyl)-11β-fluor-estra-1,3,5(10)-triene-3,17β-diol is dissolved in 60 ml of ethylmethylketone, mixed with 4.91 g of sodium iodide and stirred overnight at 90° C. For working-up, the reaction mixture is cooled to room temperature, stirred into water, extracted 3 times with ethyl acetate, washed with thiosulfate solution, dried on magnesium sulfate and concentrated by evaporation in a vacuum. 5.16 g of 11β-fluor-7α-(5-iodopentyl)-estra-1,3,5(10)-triene-3,17β-diol is obtained as a crude product, which is used without further purification in the next stage.

Workup

temperaturethe reaction mixture is cooled to room temperature
extractionextracted 3 times with ethyl acetate
washwashed with thiosulfate solution
customdried on magnesium sulfate
concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record: ord-b64eb5897bee49979225b6f967f79648
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780855B2

Reaction notes

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