Trimethylsilyl iodide → HCID 68842243, compound

HRID 2110559Notes

Reaction equation

HRID 2110559 reaction equation
[CH2:1]([C:5]1([C:18]([O:20][CH3:21])=[O:19])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[CH:7]=[C:6]1[O:16]C)[CH2:2][CH2:3][CH3:4].I[Si](C)(C)C>C(#N)C>[CH2:1]([C:5]1([C:18]([O:20][CH3:21])=[O:19])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[CH2:7][C:6]1=[O:16])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 68838210HCID 68838210, compound

Product 1

HCID 68842243HCID 68842243, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Example 1B (1 g, 3.5 mmol) in acetonitrile (5 mL) was added iodotrimethylsilane (TMSI) (0.7 mL, 5.2 mmol). The reaction solution was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo. Column chromatography on silica (ethyl acetate) afforded the title compound as a white solid (0.88 g, 92%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.47 (m, 1H), 0.68 (t, J=7.35 Hz, 3H), 0.85 (dd, J=12.32, 7.17 Hz, 1H), 1.11 (m, 2H), 2.14 (m, 1H), 2.29 (m, 1H), 3.51 (s, 3H), 5.74 (m, 1H), 7.31 (m, 1H), 7.49 (m, 1H), 7.58 (t, J=7.17 Hz, 1H), 7.93 (d, J=7.35 Hz, 1H), 12.11 (s, 1H); MS(ESI) m/z 275.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-49e37e15d13a4f5f9eda25ec7506069d
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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