Ammonium Chloride → HCID 69529940, compound

HRID 2215940Notes

Reaction equation

HRID 2215940 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12](=NNS(C3C=CC(C)=CC=3)(=O)=O)[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.C([Li])CCC.[Cl-].[NH4+]>COC(C)(C)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@:13]([CH2:15][CH2:16]3)([CH3:14])[CH:12]=[CH:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 69529278HCID 69529278, compoundHCID 178418339Butyllithium

Product 1

HCID 69529940HCID 69529940, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

2.43 g (5.37 mmol) of 3-methoxy-17-tosylhydrazono-13α-estra-1,3,5(10)-triene is suspended in 20 ml of anhydrous methyl-tert-butylether. 1.61 ml of a 10 M n-butyllithium solution in hexane is slowly added in drops to this suspension. It is stirred for 1 hour at room temperature. While being cooled, 50 ml of saturated ammonium chloride solution is added in drops. After the organic phase is separated, it is extracted with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride solution and dried (MgSO4). The crude product (2.1 g of brown oil) is chromatographed on silica gel, whereby 0.81 g of 3-methoxy-13α-estra-1,3,5(10),16-tetraene is obtained as a colorless oil; [α]D=−6° (chloroform; c=0.94).

Workup

  1. temperatureWhile being cooled
  2. customAfter the organic phase is separated
  3. extractionit is extracted with ethyl acetate
  4. washThe combined organic phases are washed with water and saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customThe crude product (2.1 g of brown oil) is chromatographed on silica gel

Sources & evidence

ORD record
ord-a10138c3887b47d39c86b50c02f4cd90
Source dataset
uspto-grants-2006_09
Patent number
US07109360B1

Reaction notes

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