[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
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%).
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