Sodium Iodide → HCID 22677988, compound

HRID 395382Notes

Reaction equation

HRID 395382 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][CH2:13][CH2:14][CH2:15]O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Na+].[I-:18]>>[I:18][CH2:15][CH2:14][CH2:13][C:12]#[C:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 5238Sodium IodideHCID 22320754HCID 22320754, compound

Product 1

HCID 22677988HCID 22677988, compound

Procedure

Preparation of the title compound with tosylated alcohol of Example 19, 5-(4-methanesulfonylphenyl)pent-4-yn-1-ol (3.14 g, 8.35 mmol), NaI (6.26 g, 41.76 mmol) following the procedure of Example 54 yielded 2.8 g (96%) of the title compound as a red oil: NMR (CDCl3) δ 2.06-2.15 (m, 2H), 2.58-2.63 (t, J=6.78, 2H), 3.04 (s, 3H), 3.33-3.37 (t, J=6.69, 2H), 7.57 (d, J=1.77, 2H), 7.85 (d, J=4.95, 2H). MS m/z 348.9 (M+H cald. for C12H13IO2S 348=349.2).

Sources & evidence

ORD record
ord-eab7c4a199fb4e78958c3ba0b766952b
Source dataset
uspto-grants-2003_08
Patent number
US06605628B1

Reaction notes

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