N-Iodosuccinimide → tert-Butyl-[4-iodo-1-(Propylcyclobutyl)but-3-enyloxy]dimethylsilane

HRID 2249572Notes

Reaction equation

HRID 2249572 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH:7]([C:11]1([CH2:15][CH2:16][CH3:17])[CH2:14][CH2:13][CH2:12]1)[CH2:8][C:9]#[CH:10])([CH3:4])([CH3:3])[CH3:2].[I:20]N1C(=O)CCC1=O>C(Cl)Cl.[H-].[Cl-].C1([Zr+2]C2C=CC=C2)C=CC=C1>[C:1]([Si:5]([O:6][CH:7]([C:11]1([CH2:15][CH2:16][CH3:17])[CH2:14][CH2:13][CH2:12]1)[CH2:8][CH:9]=[CH:10][I:20])([CH3:19])[CH3:18])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 15475299tert-Butyldimethyl-[1-(1-propylcyclobutyl)but-3-ynyloxy]silane

Product 1

HCID 53961856tert-Butyl-[4-iodo-1-(Propylcyclobutyl)but-3-enyloxy]dimethylsilaneYield 74.6%

Reagents, catalysts & solvents 2

HCID 178420592HCID 178420592, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Bis(cyclopentadienyl)zirconiumchloride hydride (3.1 g, 12.0 mmol) was added to a solution of alkyne 5 (1.7 g, 3.94 mmol) in CH2Cl2 (20 mL) at 23° C. After 0.5 h N-iodosuccinimide (2.6 g, 12.0 mmol) was added. The reaction was stirred for 0.5 h, concentrated in vacuo and the residue was diluted with pentane and washed with saturated aqueous sodium bisulfite. The organic portion was dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by FCC (silica gel, 100% pentane) gave 1.2 g (71%) of the vinyl iodide 6 as a clear, light yellow oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additionthe residue was diluted with pentane
  3. washwashed with saturated aqueous sodium bisulfite
  4. dry with materialThe organic portion was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by FCC (silica gel, 100% pentane)

Sources & evidence

ORD record
ord-d50107c863fe42329e67df39ec0a32b9
Source dataset
uspto-grants-2008_01
Patent number
US07314890B2

Reaction notes

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