6-Chloro-2-picoline → 2-(6-Chloro-2-pyridinyl)-1-(3-methyl-2-furyl)ethanone

HRID 1269063ノート

反応式

HRID 1269063 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]1[CH:14]=[CH:13][O:12][C:11]=1[C:15](OC)=[O:16].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:15]([C:11]2[O:12][CH:13]=[CH:14][C:10]=2[CH3:9])=[O:16])[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 876016-Chloro-2-picolineHCID 350231Methyl 3-methyl-2-furoateHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 184466082-(6-Chloro-2-pyridinyl)-1-(3-methyl-2-furyl)ethanone収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cold (0° C.) solution of 6-chloro-2-picoline (25.8 mL 236 mmol) and methyl 3-methyl-2-furoate (33.08 g, 236 mmol) in tetrahydrofuran (300 mL) was added lithium bis(trimethylsilyl)amide (472 mL, 1.0 M in tetrahydrofuran, 472 mmol) dropwise via a pressure equalizing funnel over 1 hour. Upon complete addition, the cold bath was removed and the resultant solution was stirred at room temperature for 15 hours. The solution was concentrated. Methanol was added to quench the reaction resulting in a yellow solid precipitating. The precipitate was collected by filteration and washed with a small amount of cold methanol. 2-(6-Chloro-2-pyridinyl)-1-(3-methyl-2-furyl)ethanone (52.2 g, 94%) was obtained as a yellow solid. 1H NMR (CDCl3): δ 7.61 (t, 1H), 7.43 (s, 1H), 7.23 (m, 2H), 6.40 (s, 1H), 4.36 (s, 2H), 2.37 (s, 3H). MS m/z 236 (M+1).

後処理

  1. customover 1 hour
  2. additionUpon complete addition
  3. customthe cold bath was removed
  4. concentrationThe solution was concentrated
  5. additionMethanol was added
  6. customto quench the reaction
  7. customresulting in a yellow solid
  8. customprecipitating
  9. customThe precipitate was collected by filteration
  10. washwashed with a small amount of cold methanol

出典と根拠

ORDレコード
ord-e3d6df7a2c8f44fdbde62e27b8170d48
出典データセット
uspto-grants-2007_04
特許番号
US07199120B2

反応ノート

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