Sodium Iodide → 1-Methylthio-4-[1[(trimethylsilyl)oxy]ethenyl]benzene

HRID 275484

Reaction equation

HRID 275484 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH3:11])=[CH:6][CH:5]=1)=[O:3].C(N(CC)CC)C.Cl[Si:20]([CH3:23])([CH3:22])[CH3:21].[I-].[Na+]>C(#N)C>[CH3:11][S:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([O:3][Si:20]([CH3:23])([CH3:22])[CH3:21])=[CH2:1])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 745011-(4-(Methylthio)phenyl)ethan-1-one

Product 1

HCID 100144611-Methylthio-4-[1[(trimethylsilyl)oxy]ethenyl]benzeneYield 101.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Under nitrogen, 11.0 g (66.2 mmol) of 4-(methylthio)acetophenone (prepared in Step 1 of Example 1) and 13.8 mL (99 mmol) of triethylamine in 50 mL of acetonitrile was treated with 12.6 mL (99.3 mmol) of chlorotrimethylsilane at ambient temperature and allowed to stir for 20 minutes prior to the slow addition of a suspension of 14.9 g (99.4 mmol) of sodium iodide in 60 mL of acetonitrile. The reaction was stirred for 3 hours, poured into ice/water, and extracted with hexane. The extracts were combined, dried (K2CO3), and concentrated in vacuo to give 16 g of crude 1-methylthio-4-[1[(trimethylsilyl)oxy]ethenyl]benzene as an oil: NMR (CDCl3) δ 0.26 (s, 9H), 2.48 (s, 3H), 4.39 (d, J=2 Hz, 1H), 4.87 (d, J=2 Hz, 1H), 7.20 (d, J=8 Hz, 2H), 7.50 (d, J=8Hz, 2H).

Workup

  1. stirringThe reaction was stirred for 3 hours
  2. extractionextracted with hexane
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34a561d356c84a0883c4bf96aeea64a1
Source dataset
uspto-grants-1995_02
Patent number
US05393790

Linked notes

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