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

HRID 1944635

Reaction equation

HRID 1944635 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a9ea7bbfe3004b4ab1736bed4c741164
Source dataset
uspto-grants-2013_03
Patent number
US08394859B2

Linked notes

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