Diiodomethane → HCID 66848997, compound

HRID 335633Notes

Reaction equation

HRID 335633 reaction equation
F[C:2](F)(F)C(O)=O.C([Zn]CC)C.ICI.[I:16][C:17](=[CH2:37])[CH2:18][C@@H:19]([CH2:28][O:29][Si:30]([CH3:36])([CH3:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[O:20][Si:21]([CH3:27])([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>ClCCCl>[I:16][C:17]1([CH2:18][C@@H:19]([CH2:28][O:29][Si:30]([CH3:36])([CH3:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[O:20][Si:21]([CH3:27])([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:2][CH2:37]1

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 86667888HCID 86667888, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 66848997HCID 66848997, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Trifluoroacetic acid (8 eq) is added to a solution of diethyl zinc (16 eq) in DCE at 0° C. and stirred for 35 mins. Diiodomethane (8 eq) is added at 0° C., and the mixture stirred for an additional 20 min. A solution of (S)-5-(2-iodoallyl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane (1 eq) in DCE is added and the reaction stirred at room temperature overnight. The reaction is quenched by addition of a mixture of methanol and brine. After stirring for an additional hour, the mixture is concentrated under reduced pressure. The crude material is extracted with aqueous NH4Cl/CHCl3 and the organic layer washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude material is triturated in hexane and the solution filtered and evaporated to afford (S)-5-((1-iodocyclopropyl)methyl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane.

Workup

  1. stirringthe mixture stirred for an additional 20 min
  2. stirringthe reaction stirred at room temperature overnight
  3. customThe reaction is quenched by addition of a mixture of methanol and brine
  4. stirringAfter stirring for an additional hour
  5. concentrationthe mixture is concentrated under reduced pressure
  6. extractionThe crude material is extracted with aqueous NH4Cl/CHCl3
  7. washthe organic layer washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material is triturated in hexane
  11. filtrationthe solution filtered
  12. customevaporated

Sources & evidence

ORD record
ord-9e6890a389834fdc97db2b36b1cb022f
Source dataset
uspto-grants-2014_11
Patent number
US08884058B2

Reaction notes

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