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Trimethylsulfonium iodide → 2-Cyclopropyl-6-(1,3-dioxolan-2-yl)pyridine

HRID 376295
ノート
印刷プレビュー

反応式

HRID 376295 の反応式
[CH2:1]([Li])CCC.[I-].C[S+](C)C.[O:11]1[CH2:15][CH2:14][O:13][CH:12]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[CH2:23])[N:17]=1>CCCCCC.O1CCCC1>[CH:22]1([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([CH:12]3[O:13][CH2:14][CH2:15][O:11]3)[N:17]=2)[CH2:1][CH2:23]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 75127Trimethylsulfonium iodideHCID 19361737HCID 19361737、化合物HCID 178418339Butyllithium

生成物 1

HCID 193617732-Cyclopropyl-6-(1,3-dioxolan-2-yl)pyridine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-15 °C

実験手順

5.60 ml of a 1.6 M solution of n-butyllithium in hexane are introduced dropwise into a suspension of 2.71 g of trimethylsulfonium iodide (13.3 mmol) in 25 ml of tetrahydrofuran cooled to -15° C. The solution is stirred at -15° C. for 20 minutes under nitrogen, and then a solution of 1.57 g of 2-[1,3]dioxolan-2-yl-6-vinylpyridine (8.90 mmol) in 5 ml of tetrahydrofuran is added dropwise. After stirring for 1 hour at -15° C., the suspension is stirred for 3 hours at room temperature. The tetrahydrofuran is evaporated off, the residue is taken up in water and the mixture is extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: hexane/ethyl acetate; 50:50). 1.24 g of a colorless oil are obtained.

後処理

  1. stirringAfter stirring for 1 hour at -15° C.
  2. stirringthe suspension is stirred for 3 hours at room temperature
  3. customThe tetrahydrofuran is evaporated off
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-bb9bf1f29cb84993b9ebc9e9b0d0a378
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06020345

反応ノート

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