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

HRID 855975

反応式

HRID 855975 の反応式
[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]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 12052TriethylsilaneHCID 614003,4-Dimethoxystyrene

生成物 1

HCID 799904-Ethyl-1,2-dimethoxybenzene収率 57%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-8aadcf4acfbb4971aadb87d91ca5d5c6
出典データセット
uspto-grants-2007_08
特許番号
US07262315B2

関連ノート

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