N-Iodosuccinimide → HCID 67035019, compound

HRID 2354093Notes

Reaction equation

HRID 2354093 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[I:9]N1C(=O)CCC1=O>C(Cl)Cl>[I:9][CH2:1][C:2]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 1380828822428-85-9

Product 1

HCID 67035019HCID 67035019, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methylenecyclohexanol (1.88 g) in CH2Cl2 (37.6 mL) was added N-iodosuccinimide (4.5 g) under nitrogen atmosphere, which was stirred at ambient temperature for 3 hours. The resultant was washed with Na2S2O3 aq., H2O, and brine. The organic phase was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give 1-(iodomethyl)-7-oxabicyclo[2.2.1]heptane (1.5 g) as colorless oil.

Workup

  1. washThe resultant was washed with Na2S2O3 aq., H2O, and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c3bf2cdcacfb4b2db56473b55a35f981
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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