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

HRID 33948

반응식

HRID 33948 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 (slilica 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 (slilica gel, 1:99 EtOAc:Hexanes)

출처 및 근거

ORD 기록
ord-7d06dbbb8e7b4673802ee94161a74626
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429681B2

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