Sodium hydride → HCID 24771795, compound

HRID 2221428Notes

Reaction equation

HRID 2221428 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][C:10]1([CH3:23])[C:14]([CH3:15])=[CH:13][CH2:12][CH:11]1[C:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH:17]=1>CS(C)=O.C(OCC)C>[CH3:9][C:10]1([CH3:23])[C:14]([CH3:15])=[CH:13][CH2:12][CH:11]1[C:16]1[CH2:21][CH2:20][C:19]2([O:22][CH2:2]2)[CH2:18][CH:17]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 58769693HCID 58769693, compound

Product 1

HCID 24771795HCID 24771795, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Trimethylsulfoxonium iodide (4.78 g, 21.63 mmol.) is added in portions to a suspension of sodium hydride (60% in mineral oil, 1.00 g, 25.54 mmol.) in DMSO (10 ml). Stirring is carried out for 30 minutes before 4-(2,2,3-trimethyl-cyclopent-3-enyl)-cyclohex-3-enone (XIII, see U.S. Pat. No. 5,189,013, 2.78 g, 13.64 mmol.), dissolved in DMSO (10 ml), is added. When the addition is complete, stirring is continued for a further 30 minutes, and then the reaction solution is poured onto ice (25 ml). The mixture is diluted with diethyl ether (50 ml), the phases are separated, and the aqueous phase is extracted three times with diethyl ether (50 ml each time). The combined organic phases are washed once with saturated NaCl solution before being dried over Na2SO4, filtered off and concentrated in a rotary evaporator. 3.08 g of crude product are obtained, which is then purified by flash chromatography (cyclohexane/EtOAc=20:1, Rf=0.22). 2.21 g of a colourless oil are obtained.

Workup

  1. additionis added
  2. additionWhen the addition
  3. stirringstirring
  4. additionthe reaction solution is poured onto ice (25 ml)
  5. customthe phases are separated
  6. extractionthe aqueous phase is extracted three times with diethyl ether (50 ml each time)
  7. washThe combined organic phases are washed once with saturated NaCl solution
  8. dry with materialbefore being dried over Na2SO4
  9. filtrationfiltered off
  10. concentrationconcentrated in a rotary evaporator
  11. custom3.08 g of crude product are obtained
  12. customwhich is then purified by flash chromatography (cyclohexane/EtOAc=20:1, Rf=0.22)

Sources & evidence

ORD record
ord-9a0f35d7e470466e92ef506301465c5d
Source dataset
uspto-grants-2008_05
Patent number
US07368613B2

Reaction notes

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