Ethyl Bromide → 7-Ethoxy-2-methylquinoline

HRID 339049ノート

反応式

HRID 339049 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH3:21]>CN1C(=O)CCC1>[CH2:20]([O:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1)[CH3:21]

参加物

5

反応物 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 1354519692-Methylquinolin-7-ol

生成物 1

HCID 867075387-Ethoxy-2-methylquinoline収率 88.5%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To a stirred mixture of 2-methylquinolin-7-ol (400 mg, 2.51 mmol), Cs2CO3 (2.46 g, 7.54 mmol) and NMP (12 mL) was added bromoethane (0.563 mL, 7.54 mmol). The reaction mixture was stirred at ambient temperature overnight. The reaction was partitioned between ether and water. The aqueous layer was extracted with ether. The combined organic layers were washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (2:1 to 5:1 hexanes:EtOAc) to give 7-ethoxy-2-methylquinoline (416 mg, 88%).

後処理

  1. customThe reaction was partitioned between ether and water
  2. extractionThe aqueous layer was extracted with ether
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (2:1 to 5:1 hexanes:EtOAc)

出典と根拠

ORDレコード
ord-10c8578d969a46b094202a0b360964fb
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

読み込み中…