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

HRID 1598358

反応式

HRID 1598358 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c90bde218b294df7b5f32a0c62177e6d
出典データセット
uspto-grants-1998_04
特許番号
US05736579

関連ノート

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