Methanol → HCID 86702161、化合物

HRID 1776238ノート

反応式

HRID 1776238 の反応式
[CH3:1][C:2]([N:6]1[CH2:10][CH2:9][CH2:8][S:7]1(=[O:12])=[O:11])([C:4]#[CH:5])[CH3:3].C[OH:14]>S(=O)(=O)(O)O.[Hg]=O>[O:11]=[S:7]1(=[O:12])[CH2:8][CH2:9][CH2:10][N:6]1[C:2]([CH3:1])([CH3:3])[C:4](=[O:14])[CH3:5]

参加物

5

反応物 2

HCID 887MethanolHCID 64005706HCID 64005706、化合物

生成物 1

HCID 86702161HCID 86702161、化合物収率 43%

試薬・触媒・溶媒 2

HCID 30856Mercuric oxide触媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-(2-methylbut-3-yn-2-yl)isothiazolidine-1,1-dioxide (3.500 g, 18.7 mmol) and mercury(II) oxide (0.810 g, 3.7 mmol) in methanol (100 mL) and 2 N aqueous sulfuric acid (50 mL) was heated at 90° C. for 3 hrs. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo. The residue was treated with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford the desired product as a yellow oil (1.65 g, 43%). 1H NMR (300 MHz, CDCl3) δ 3.38 (t, 2H, J=6.6 Hz), 3.21 (t, 2H, J=7.5 Hz), 2.42-2.30 (m, 2H), 2.28 (s, 3H), 1.60 (s, 6H).

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe residue was treated with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried (anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-c32f8fc8928346cb9b18d9a753470274
出典データセット
uspto-grants-2016_02
特許番号
US09265772B2

反応ノート

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