Butyl iodide → 1h-Indole,7-butoxy-

HRID 401610

反応式

HRID 401610 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH2:19][CH2:20][CH3:21]>C(C(C)=O)C>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2)[CH2:19][CH2:20][CH3:21]

参加物

5

反応物 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 27376517-Hydroxyindole

生成物 1

HCID 219401081h-Indole,7-butoxy-収率 90%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

反応条件

温度
55 °C

実験手順

To a stirred solution of 7-hydroxyindole and potassium carbonate (325 mg, 2.35 mmol) in methyl ethyl ketone (2.4 mL) was added iodobutane (1.24 mL, 10.8 mmol) at room temperature. After the mixture was heated at 55° C. for 12 h the solvent was removed and water was added. The mixture was extracted with EtOAc (3 times), dried over anhydrous MgSO4, filtered and evaporated. After chromatographic purification on silica gel, 7-n-butoxyindole was obtained in 90% yield (310 mg). 1H NMR (500 MHz, CDCl3) δ 8.39 (1H, brs), 7.23 (1H, d, J=8.0 Hz, 7.17 (1H, t, J=3.0 Hz), 7.01 (1H, t, J=7.5 Hz), 6.63 (1H, d, J=7.0 Hz), 6.53 (1H, t, J=2.5 Hz), 4.14 (2H, t, J=5.2 Hz), 1.88-1.80 (2H, m), 1.59-1.50 (2H, m), 1.00 (3H, t, J=7.0 Hz).

後処理

  1. customwas removed
  2. additionwater was added
  3. extractionThe mixture was extracted with EtOAc (3 times)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customAfter chromatographic purification on silica gel

出典と根拠

ORDレコード
ord-d988c511e2c34a64b46759f49c0e3aa1
出典データセット
uspto-grants-2014_06
特許番号
US08741942B2

関連ノート

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