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Methyl iodide → 3-(5-((methylthio)methyl)furan-2-yl)pyridine

HRID 1913349
ノート
印刷プレビュー

反応式

HRID 1913349 の反応式
[C:1](=O)([S:3][CH2:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)C.C[O-].[Na+].CI.C(=O)(O)[O-].[Na+]>CO>[CH3:1][S:3][CH2:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 11993872S-(5-(Pyridin-3-yl)furan-2-yl)methyl ethanethioate

生成物 1

HCID 119938733-(5-((methylthio)methyl)furan-2-yl)pyridine収率 54%

試薬・触媒・溶媒 1

HCID 887Methanol
溶媒
3 回

実験手順

(See FIG. 7.) To a solution of 13 (27 mg, 0.12 mmol) in anhydrous CH3OH (3 mL) at 0° C. under argon was added a solution of sodium methoxide (15 mg, 0.28 mmol) in anhydrous CH3OH (1 mL) dropwise, over 10 min and the resultant solution was stirred for 30 min. To the solution was added methyl iodide (17 μL, 0.28 mmol) in anhydrous CH3OH (1 mL) dropwise over 1 min and the resultant solution was stirred for 30 min. The reaction was stopped by the addition of aqueous sodium bicarbonate (satd. soln., 10 mL). The CH3OH was removed in vacuo and the aqueous fraction was extracted with EtOAc (3×10 mL). The combined organic fractions were dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.2) to afford the title compound 15 (13 mg, 54% yield) as an off white solid: mp=67-68° C.; 1H NMR (CDCl3) δ 8.90 (br s, 1H), 8.46 (m, 1H), 7.90 (m, 1H), 7.29 (m, 1H), 6.66 (d, J=3.3 Hz, 1H), 6.29 (d, J=3.3 Hz, 1H), 3.74 (s, 2H), 2.14 (s, 3H); LRMS (ESI) m/z calcd for C11H12NOS [M+H]+ 206. found 206.

後処理

  1. customThe CH3OH was removed in vacuo
  2. extractionthe aqueous fraction was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.2)

出典と根拠

ORDレコード
ord-3d710a995b4e42999e5f51094cc7427a
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08609708B2

反応ノート

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