Diethyl Ether → 4-Ethyl-1,2-dimethoxybenzene

HRID 855975

Reaction equation

HRID 855975 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[CH2:7].C([SiH](CC)CC)C.C(OCC)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH3:7])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12052TriethylsilaneHCID 614003,4-Dimethoxystyrene

Product 1

HCID 799904-Ethyl-1,2-dimethoxybenzeneYield 57%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

In a 5 mL flask opened to the air, to a clear solution of 3,4-dimethoxystyrene (100 μL, 0.755 mmol) in benzene (0.8 mL) was added triethylsilane (240 μL, 0.816 mmol). The flask was placed in a 60° C. bath and iodo[bis(triphenylphosphine)]dioxorhenium(V) (32 mg, 0.037 mmol) was added. The resulting brown solution was heated at 60° C. for 12 hours. The crude reaction mixture was directly applied to a SiO2 column and chromatographed eluting with 4:1 hexanes:diethyl ether to afford 3,4-dimethoxyethylbenzene (52 mg, 57% yield) as a colorless liquid. The reaction was repeated using pent-2-enal and t-butyl acrylate as the electrophilic reactants, as indicated in the first two schemes above (wherein “TES” represents triethylsilyl).

Workup

  1. customwas placed in a 60° C.
  2. customThe crude reaction mixture
  3. customchromatographed
  4. washeluting with 4:1 hexanes

Sources & evidence

ORD record
ord-8aadcf4acfbb4971aadb87d91ca5d5c6
Source dataset
uspto-grants-2007_08
Patent number
US07262315B2

Linked notes

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