Sulfoxonium, trimethyl-, iodide (1:1) → Methyl 2-(1-methylcyclopropyl)quinoline-6-carboxylate

HRID 1094655ノート

反応式

HRID 1094655 の反応式
[I-].C[S+](C)(C)=O.[CH3:7]C(C)([O-])C.[K+].[C:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:26]([O:28][CH3:29])=[O:27])[CH:22]=2)[N:17]=1)([CH3:15])=[CH2:14]>CS(C)=O.C1COCC1.C1COCC1>[CH3:29][O:28][C:26]([C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([C:13]1([CH3:7])[CH2:15][CH2:14]1)[CH:25]=[CH:24]2)=[O:27]

参加物

6

反応物 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 66637151Methyl 2-isopropenylquinoline-6-carboxylate

生成物 1

HCID 66636963Methyl 2-(1-methylcyclopropyl)quinoline-6-carboxylate収率 68.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21830753dimethylsulfoxide THF溶媒

実験手順

To a stirred suspension of trimethylsulfoxonium iodide (435 mg, 2.06 mmol) in dimethylsulfoxide-THF (3 ml-2 ml) was added potassium t-butoxide (231 mg, 2.06 mmol) in one portion at ambient temperature. After 30 min. at same temperature, to this (colorless solution) was added a solution of methyl 2-isopropenylquinoline-6-carboxylate (312 mg, 1.37 mmol) in THF (3 ml) at room temperature. The mixture was stirred at room temperature for 40 min then 1 hour at 60° C. The mixture was quenched with water and diluted with ethyl acetate-toluene (8:1) (90 ml). The organic solution was separated and washed with water (×2), brine, dried over sodium sulfate and concentrated in vacuo to crude product. The crude product was purified by column chromatography on silica gel (250 g) with hexane-ethyl acetate (10:1) to furnish the title compound (225 mg, 68%) as a white solid. 1H NMR (270 MHz, CDCl3) δ ppm 0.91-0.98 (2H, m), 1.38-1.45 (2H, m), 1.64 (3H, s), 3.98 (3H, s), 7.42-7.48 (1H, m), 7.97-8.27 (3H, m), 8.50-8.55 (1H, m). MS (ESI): m/z 242.15 (M+H)+.

後処理

  1. custom1 hour
  2. customat 60° C
  3. customThe mixture was quenched with water
  4. additiondiluted with ethyl acetate-toluene (8:1) (90 ml)
  5. customThe organic solution was separated
  6. washwashed with water (×2), brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo to crude product
  9. customThe crude product was purified by column chromatography on silica gel (250 g) with hexane-ethyl acetate (10:1)

出典と根拠

ORDレコード
ord-403c74f9213d4d1aa9a0fdf33ce7a822
出典データセット
uspto-grants-2012_03
特許番号
US08134004B2

反応ノート

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