Diiodomethane → HCID 66849204, compound

HRID 929454Notes

Reaction equation

HRID 929454 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 86667885HCID 86667885, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 66849204HCID 66849204, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Trifluoroacetic acid (TFA; 281 mg, 2.47 mmol) was added to a solution of diethyl zinc (ZnEt2, 2.5 mL, 2.5M in hexane) in DCE (1 mL) at 0° C. and stirred for 35 mins. Diiodomethane (CH2I2, 66 mg, 2.5 mmol) was then added at 0° C., and the mixture stirred for an additional 20 min. A solution of (R)-5-(2-iodoallyl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane (step D; 188 mg, 0.41 mmol) in DCE (2 ml) was added and the reaction stirred at room temperature overnight. The reaction was then quenched by addition of a mixture of methanol (5 mL) and brine (0.5 mL). After stirring for an additional hour, the mixture was concentrated under reduced pressure. The crude material was extracted with aq.NH4Cl/CHCl3 and the organic layer washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude material was triturated in hexane and the solution filtered and evaporated to afford (R)-5-((1-iodocyclopropyl)methyl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane (148 mg, 77%).

Workup

  1. stirringthe mixture stirred for an additional 20 min
  2. stirringthe reaction stirred at room temperature overnight
  3. customThe reaction was then quenched by addition of a mixture of methanol (5 mL) and brine (0.5 mL)
  4. stirringAfter stirring for an additional hour
  5. concentrationthe mixture was concentrated under reduced pressure
  6. extractionThe crude material was extracted with aq
  7. washNH4Cl/CHCl3 and the organic layer washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was triturated in hexane
  11. filtrationthe solution filtered
  12. customevaporated

Sources & evidence

ORD record
ord-6b8f5e9b279b4827a5a6b330300fc4a3
Source dataset
uspto-grants-2016_03
Patent number
US09296686B2

Reaction notes

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