Acetonitrile → 3-Acetoxy-7alpha-(11-acetoxyundecyl)-1,3,5(10)-estratrien-17-one

HRID 1885558Notes

Reaction equation

HRID 1885558 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:33][C:32]2[C@H:27]([CH2:28][CH2:29][C:30](=[O:34])[CH:31]=2)[C@@H:26]2[C@@H:17]1[C@H:18]1[C@@:22]([CH2:24][CH2:25]2)([CH3:23])[C:21](=[O:35])[CH2:20][CH2:19]1)(=[O:3])[CH3:2].[Br-].[Li+].[C:38](=[O:41])(O)[O-].[Na+].[C:43](#N)C>[Cu](Br)Br>[C:38]([O:34][C:30]1[CH:29]=[CH:28][C:27]2[C@@H:26]3[C@H:17]([C@H:18]4[C@@:22]([CH2:24][CH2:25]3)([CH3:23])[C:21](=[O:35])[CH2:20][CH2:19]4)[C@H:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:33][C:32]=2[CH:31]=1)(=[O:41])[CH3:43]

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 57202929HCID 57202929, compound

Product 1

HCID 150861223-Acetoxy-7alpha-(11-acetoxyundecyl)-1,3,5(10)-estratrien-17-one

Reagents, catalysts & solvents 1

HCID 24611Copper bromide (CuBr2)Catalyst

Procedure

10.5 g of 7α-(11-acetoxyundecyl)-4-estrene-3,17-dione in 58.5 ml of acetonitrile is added to a solution of 9.1 g of copper(II) bromide and 1.78 g of lithium bromide in 141 ml of acetonitrile and heated under reflux for 0.5 hour. Then the mixture is cooled to 0°, gradually combined with 235 ml of sodium bicarbonate solution, extracted three times with ethyl acetate, washed with water and sodium chloride solution, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, thus obtaining 7.5 g of 3-acetoxy-7α-(11-acetoxyundecyl)-1,3,5(10)-estratrien-17-one, [α]D =75.8°, as an oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 0.5 hour
  3. temperatureThen the mixture is cooled to 0°
  4. extractionextracted three times with ethyl acetate
  5. washwashed with water and sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness under vacuum
  8. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-894a2cbc5d2a499d9fa7a81ebe45fe47
Source dataset
uspto-grants-1992_09
Patent number
US05145847

Reaction notes

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