Trimethylsilyl iodide → [1-(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydronaphthalen-1-yl]methyl Acetate

HRID 494661Notes

Reaction equation

HRID 494661 reaction equation
[C:1]([O:4][CH2:5][C:6]1([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[CH:8]=[C:7]1[O:17]C)(=[O:3])[CH3:2].I[Si](C)(C)C>C(#N)C>[C:1]([O:4][CH2:5][C:6]1([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[CH2:8][C:7]1=[O:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 68873688[2-methoxy-1-(3-methylbutyl)-4-oxo-1,4-dihydronaphthalen-1-yl]methyl Acetate

Product 1

HCID 68872021[1-(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydronaphthalen-1-yl]methyl AcetateYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Example 179C (0.12 g, 0.38 mmol) in acetonitrile (3.5 mL) was added iodotrimethylsilane (TMSI) (81 μL, 0.57 mmol). The reaction solution was stirred at room temperature for 3 h. After which, additional 1.5 equivalents of TMSI (81 μL) were added and stirring was continued for 2 h. The solution was quenched with water (3 mL) and extracted with ethyl acetate (2× 5 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (70% ethyl acetate/hexane) afforded product as a white solid (91%). 1H NMR (300 MHz, CDCl3) δ ppm 0.55 (s, 1H), 0.77 (m, 12H), 0.93 (m, 2H), 1.36 (m, 3H), 1.79 (m, 8H), 2.19 (m, 3H), 3.77 (m, 2H), 4.42 (d, J=11.03 Hz, 1H), 4.57 (m, 3H), 6.15 (s, 1H), 7.46 (m, 4H), 7.59 (m, 1H), 7.69 (m, 1H), 8.12 (m, 2H); MS m/z 303.0.

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe solution was quenched with water (3 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-5e7f1f35dccb4ad2b1af84033fc896e1
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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