Potassium Carbonate → 6-Methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene

HRID 643911Notes

Reaction equation

HRID 643911 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9](O)[CH:8]([CH3:14])[CH2:7][CH2:6]2.C([SiH](CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH3:14])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 66750495HCID 66750495, compound

Product 1

HCID 216367206-Methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxy-2-methyl-1,2,3,4-tetrahydronaphthalen-1-ol (8.24 g) and triethylsilane (9.2 mL, 74 mmol) in DCM (100 mL) at 0° C. is added boron trifloride-diethyl etherate (17.6 mL, 110 mmol) drop wise. After stirring for 10 min, the mixture is warmed to RT and stirred for 30 min. 10% K2CO3 solution is added and it is extracted with EtOAc. The organic layer is washed with brine, dried with MgSO4 and concentrated to give the title compound as a yellow oil, which is then used in the next step without purification.

Workup

  1. stirringstirred for 30 min
  2. extractionit is extracted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1fdae06a89a04b1c982ad87416d70fe3
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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