Isopropyl iodide → 5-Isopropoxyquinoline

HRID 2204205ノート

反応式

HRID 2204205 の反応式
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].I[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[CH:19]([O:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2)([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 135441757Quinolin-5-ol

生成物 1

HCID 585508625-Isopropoxyquinoline収率 91%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a mixture of quinolin-5-ol (2.00 g, 13.8 mmol) and K2CO3 (7.62 g, 55.1 mmol) in DMF (20 mL) was added 2-iodopropane (2.76 mL, 27.6 mmol). The reaction mixture was heated at 80° C. overnight before it was partitioned between EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4 and concentrated to dryness. The crude material was purified by column chromatography (10-20% EtOAc-Hex) to provide 5-isopropoxyquinoline (91%) as a light yellow oil. ESI-MS m/z calc 187.1, found 188.3 (M+1)+. Retention time: 1.06 minutes (3 min run).

後処理

  1. customwas partitioned between EtOAc and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe crude material was purified by column chromatography (10-20% EtOAc-Hex)

出典と根拠

ORDレコード
ord-e574e9a5e16f4481b6b95bd0a0562e1d
出典データセット
uspto-grants-2016_06
特許番号
US09365588B2

反応ノート

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