Sodium Iodide → HCID 178506582, compound

HRID 1369444Notes

Reaction equation

HRID 1369444 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:18].[Na+]>CC(C)=O.C(OCC)C>[CH2:1]([O:8][C@H:9]1[CH2:12][C@H:11]([I:18])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 178505331HCID 178505331, compound

Product 1

HCID 178506582HCID 178506582, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of cis-3-benzyloxy-1-methanesulfonyloxycyclobutane (1.25 g, 4.8 mmol) and sodium iodide (2.16 g, 14.4 mmol) in dry acetone (20 ml) was refluxed under nitrogen for 3.5 days. The mixture was cooled and diluted with diethyl ether (150 ml). The suspension was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and filtered through a plug of silica gel, eluting with ethyl acetate to give trans-3-benzyloxy-1-iodocyclobutane (1.19 g, 86%) as an orange oil; 1H NMR (250 MHz, CDCl3) δ2.54-2.65 (2H, m), 2.94-3.04 (2H, m), 3.85-4.06 (2H, m), 4.40 (2H, s), 7.26-7.38 (5H1 m).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. filtrationfiltered through a plug of silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-88a9aceb89a44f6d9f7da0692bde6a2a
Source dataset
uspto-grants-2003_06
Patent number
US06579875B1

Reaction notes

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