Dimethylformamide → 3-Iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine

HRID 84464

反応式

HRID 84464 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[I:8].[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10]1.O1CCCC1.CN(C)C=O.[H-].[Na+]>O>[I:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[O:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][S:9][CH:10]=1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 83731Thiophene-3-ethanolHCID 27631634-Chloro-3-iodopyridine

生成物 1

HCID 579002113-Iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine収率 81%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 4-chloro-3-iodo-pyridine (4.79 g, 20.0 mmol) and 2-(3-thienyl)ethanol (2.43 mL, 22.0 mmol) in a mixture of tetrahydrofuran (60 mL, 700 mmol) and N,N-dimethylformamide (20 mL, 200 mmol) was added sodium hydride, 60% dispersion in mineral oil (0.960 g, 24.0 mmol) portionwise over 30 min. The mixture was stirred for 2 hours, poured carefully into 200 ml of cold water and extracted with diethylether twice. The organic extract was washed with water and brine, and dried over MgSO4. After concentration under vacuum, the crude residue was purified on silica gel column, eluting with 50% ethyl acetate in hexane to give 3-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine (yield 5.34 g, 81%). 1H NMR (400 MHz, CDCl3) δ 8.75 (s, 1H), 8.35 (d, J=5.6, 1H), 7.29 (dd, J=3.0, 4.8, 1H), 7.19 (s, 1H), 7.12 (d, J=4.9, 1H), 6.70 (d, J=5.6, 1H), 4.26 (t, J=6.5, 2H), 3.21 (t, J=6.5, 2H). MS (ESI+) 332.0, 221.9.

後処理

  1. extractionextracted with diethylether twice
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationAfter concentration under vacuum
  6. customthe crude residue was purified on silica gel column
  7. washeluting with 50% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-c9a50cfa59594005bbfad5c0ea478f83
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

関連ノート

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