Imidazole → 8-Iodo-1,4-dioxaspiro[4.5]decane

HRID 1468766Notes

Reaction equation

HRID 1468766 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8](O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:36]I.S([O-])(O)=O.[Na+]>O1CCCC1>[I:36][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 23665763Sodium Bisulfite

Product 1

HCID 110218798-Iodo-1,4-dioxaspiro[4.5]decaneYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1,4-dioxa-spiro[4.5]decan-8-ol (18.0 g, 114 mmol), imidazole (10.1 g, 148 mmol) and triphenylphosphine (34.3 g, 131 mmol) in tetrahydrofuran (57 ml) was added iodine (33.2 g, 131 mmol) in tetrahydrofuran (57 ml) at 0° C. The mixture was warmed to room temperature, and stirred for 6 hours. The mixture was poured into 10 wt % aqueous sodium hydrogen sulfite, and the organic compound was extracted with hexane (three times). The organic layer was washed with water, dried over sodium sulfate, and concentrated in vacuo. The residue was dissolved into hexane again, and filtrated to remove triphenylphosphine oxide. The filtrate was concentrated in vacuo to afford 8-iodo-1,4-dioxa-spiro[4.5]decane as a colorless oil (18.1 g, 67.6 mmol, 59%).

Workup

  1. extractionthe organic compound was extracted with hexane (three times)
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved into hexane again
  6. filtrationfiltrated
  7. customto remove triphenylphosphine oxide
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-82c636fcf7394fcf8f28c91d88cba720
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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