Trimethylsilyl iodide → Methyl 1-(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydronaphthalene-1-carboxylate

HRID 494657Notes

Reaction equation

HRID 494657 reaction equation
C[O:2][C:3]1[C:4]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])([C:14]([O:16][CH3:17])=[O:15])[C:5]2[C:10]([C:11](=[O:13])[CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.I[Si](C)(C)C>C(#N)C>[CH3:21][CH:20]([CH3:22])[CH2:19][CH2:18][C:4]1([C:14]([O:16][CH3:17])=[O:15])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11](=[O:13])[CH2:12][C:3]1=[O:2]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 68842102Methyl 2-methoxy-1-(3-methylbutyl)-4-oxo-1,4-dihydronaphthalene-1-carboxylate

Product 1

HCID 68839914Methyl 1-(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydronaphthalene-1-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Example 178B (0.18 g, 0.6 mmol) in acetonitrile (2 mL) was added iodotrimethylsilane (TMSI) (0.13 mL, 0.9 mmol). The reaction solution was stirred at room temperature for 3 h. After which, additional 1.5 equivalents of TMSI (0.13 mL) were added and stirring was continued for 2 h. The solution was quenched with water (5 mL) and extracted with ethyl acetate (2× 5 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (40%-80% ethyl acetate/hexane) afforded product as a white solid (0.11 g, 65%). 1H NMR (300 MHz, CDCl3) δ ppm 0.46 (m, 1H), 0.79 (m, 7H), 1.41 (m, 1H), 2.29 (m, 1H), 2.53 (m, 1H), 3.60 (s, 3H), 3.83 (m, 1H), 6.11 (s, 1H), 7.52 (m, 3H), 8.12 (d, J=7.72 Hz, 1H); MS m/z 289.0 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe solution was quenched with water (5 mL)
  4. extractionextracted with ethyl acetate (2× 5 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-881a58b289fd41daad00598257a2b5b6
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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