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Diiodomethane → HCID 66848997, compound

HRID 929461
Notes
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Reaction equation

HRID 929461 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-Dichloroethane
Solvent
2×

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-0d6d28e659114014a015c48a1bd585c8
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296686B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes