2-Bromopropane → 5-Isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene

HRID 1944635

반응식

HRID 1944635 반응식
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]=1[OH:13].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:21]([CH3:23])[CH3:22]>CC(C)=O>[CH:21]([O:13][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9]2)([CH3:23])[CH3:22]

참가 물질

5

반응물 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 574358992-Methoxy-5,6,7,8-tetrahydronaphthalen-1-ol

생성물 1

HCID 574359005-Isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene수율 93%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

33 (4.55 g, 25.5 mmol) was charged in a 250 mL round bottom flask, equipped with a reflux condenser, under nitrogen gas. 50 mL of anhydrous acetone was added followed by cesium carbonate (66.55 g, 204.3 mmol). 2-bromopropane (23.94 mL, 255.0 mmol) was added and the reaction mixture was refluxed for 12 h. The solvent was filtered and evaporated in vacuo and purified by flash column chromatography (silica gel, 1:99 EtOAc:Hexanes) to afford 5.2 g (93%) of 5-isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene (34). Rf value: 0.615 (15:85 EtOAc:Hexanes).

후처리

  1. customequipped with a reflux condenser, under nitrogen gas
  2. temperaturethe reaction mixture was refluxed for 12 h
  3. filtrationThe solvent was filtered
  4. customevaporated in vacuo
  5. custompurified by flash column chromatography (silica gel, 1:99 EtOAc:Hexanes)

출처 및 근거

ORD 기록
ord-a9ea7bbfe3004b4ab1736bed4c741164
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394859B2

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