N-Iodosuccinimide → HCID 86599786, compound

HRID 406809Notes

Reaction equation

HRID 406809 reaction equation
[S:1]1[C:5]([CH2:6][CH:7]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C:8]#[CH:9])=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2.[I:22]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>ClCCl>[S:1]1[C:5]([CH2:6][CH:7]([O:10][Si:11]([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:12])[CH3:13])/[CH:8]=[CH:9]/[I:22])=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 86599785HCID 86599785, compound

Product 1

HCID 86599786HCID 86599786, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cp2ZrHCl (1.719 g, 6.67 mmol) was added to a solution of 9-5 (1.372 g, 4.34 mmol) in dichloromethane (30 mL). The reaction was stirred for 30 min. at room temperature and N-iodosuccinimide (1.997 g, 8.88 mmol) was added. After 1 h, the reaction was poured into 100 mL of saturated NaHCO3 solution. The resulting mixture was extracted with dichloromethane (3×75 mL) and the combined organic extracts were dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (2% ethyl acetate/hexanes) gave 9-6 (1.7484 g, 91%).

Workup

  1. waitAfter 1 h
  2. extractionThe resulting mixture was extracted with dichloromethane (3×75 mL)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (2% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e8b67e3e2e1b44858acdf125c6711328
Source dataset
uspto-grants-2014_06
Patent number
US08754122B2

Reaction notes

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