Ethyl Bromide → 7-Ethoxy-2-methylquinoline

HRID 339049노트

반응식

HRID 339049 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 867075387-Ethoxy-2-methylquinoline수율 88.5%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-10c8578d969a46b094202a0b360964fb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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