Sulfoxonium, trimethyl-, iodide (1:1) → HCID 69789289, compound

HRID 1815780Notes

Reaction equation

HRID 1815780 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[CH3:7][O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH:17]=[CH:16]4)[C@H:13]([CH3:28])[CH2:12][C:11]=2[CH:10]=1>CS(C)=O>[CH3:7][O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[C@H:17]3[CH2:2][C@@H:16]43)[C@H:13]([CH3:28])[CH2:12][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 69789972HCID 69789972, compound

Product 1

HCID 69789289HCID 69789289, compoundYield 131.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

—Sodium hydride (60% suspension in mineral oil, 1.15 g) was added to a suspension of trimethylsulfoxonium iodide (5.57 g) in dry dimethyl sulfoxide (115 ml) and the mixture was stirred at room temperature for 20 min. (7α,14β)-3-Methoxy-7-methylestra-1,3,5(10),15-tetraen-17-one (Example 7, step iv; 1.92 g) was added and stirring was continued for 1.5 h. The reaction mixture was poured into ice-water and the product was extracted into ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure, to give (7α,14β,15β,16β)-3-methoxy-7-methyl-15,16-methyleneestra-1,3,5(10)-trien-17-one (2.65 g). The product was used in the following step without further purification.

Workup

  1. additionwas added
  2. extractionthe product was extracted into ethyl acetate
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d63db76b45549bbb711972f431cfba9
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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