N-Iodosuccinimide → HCID 21705995, compound

HRID 1024112Notes

Reaction equation

HRID 1024112 reaction equation
[CH2:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)[CH:2]=[CH2:3].[I:9]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C1COCC1>[I:9][CH2:3][CH2:2][CH2:1][C:4]1[S:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 6423302-allylthiophene

Product 1

HCID 21705995HCID 21705995, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Cp2ZrHCl (9.141 g, 35.4 mmol) was added to a solution of 33 (3.668 g, 29.5 mmol) in THF (50 mL). The mixture was stirred for 1.5 h at 40° C., cooled to 0° C. and was then treated with N-iodosuccinimide (NIS, 7.972 g, 35.4 mmol). The reaction was allowed to warm to room temperature and after 75 min., 100 mL of saturated NaHCO3 solution was added. The mixture was extracted with ether (2×100 mL) and the combined ether solution was dried (Na2SO4), filtered and evaporated. The residue was purified on a Teledyne Isco Combiflash unit (330 g silica gel column, 0%→20% ethyl acetate/hexanes) which gave the title compound (4.558 g, 18.1 mmol, 61%).

Workup

  1. temperaturecooled to 0° C.
  2. temperatureto warm to room temperature and after 75 min.
  3. extractionThe mixture was extracted with ether (2×100 mL)
  4. dry with materialthe combined ether solution was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a Teledyne Isco Combiflash unit (330 g silica gel column, 0%→20% ethyl acetate/hexanes) which

Sources & evidence

ORD record
ord-958c2eb54cb64915895c79407162a972
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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