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

HRID 1598358

Reaktionsgleichung

Reaktionsgleichung von HRID 1598358
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 100144611-Methylthio-4-[1[(trimethylsilyl)oxy]ethenyl]benzeneAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

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) δ0.26 (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=8 Hz, 2H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c90bde218b294df7b5f32a0c62177e6d
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05736579

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