Potassium Iodide → HCID 69589733, compound

HRID 890905Notes

Reaction equation

HRID 890905 reaction equation
Br[CH2:2][CH2:3][CH2:4]O.[CH3:6][C@@:7]12[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C@@H:11]1[CH2:17][CH2:18][C:19]3[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=3[C@H:10]1[CH2:9][CH2:8]2.[OH-:26].[Na+].[I-].[K+]>CO.O.C(Cl)Cl>[OH:26][CH:3]([CH3:4])[CH2:2][O:25][C:23]1[CH:22]=[CH:21][C:20]2[C@@H:10]3[C@H:11]([C@H:12]4[C@@:7]([CH2:8][CH2:9]3)([CH3:6])[C:15](=[O:16])[CH2:14][CH2:13]4)[CH2:17][CH2:18][C:19]=2[CH:24]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 5870EstroneHCID 123083-Bromo-1-propanolHCID 14798Sodium Hydroxide

Product 1

HCID 69589733HCID 69589733, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-1-propanol (0.400 ml, 4.42 mmol), (+)-estrone (1.00 g, 3.70 mmol), sodium hydroxide (150 mg, 3.75 mmol) and potassium iodide (100 mg, 0.602 mmol) in 10 ml methanol and 10 ml water was refluxed overnight. The reaction mixture was shaken with 100 ml methylene chloride and 100 ml water. The organic layer was washed with a 10% NaHCO3 solution (100 ml×2) and water (100 ml×2) before drying over anhydrous Na2SO4. Further purification was performed by silica gel column chromatography with methylene chloride: acetone (50:1) as the eluent to yield 3-(2-hydroxy-propoxy)-estra-1,3,5(10)-trien-17-one (800 mg, 66%). 1H NMR spectral data, 6(CDCl3): 0.93–2.94 (m, 23H on estrone), 3.88 (2H, —CH2OH), 4.13 (t, 2H, estrone-OCH2—), 6.68–7.23 (m, 3H, aromatics).

Workup

  1. washThe organic layer was washed with a 10% NaHCO3 solution (100 ml×2) and water (100 ml×2)
  2. dry with materialbefore drying over anhydrous Na2SO4
  3. customFurther purification

Sources & evidence

ORD record
ord-ef2e33358ff94e3cacbdeb54c0a7386c
Source dataset
uspto-grants-2006_02
Patent number
US07001648B2

Reaction notes

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