2-Bromo-3-methylthiophene → 2-(2-Methoxy-ethyl)-3-methyl-thiophene

HRID 1696731ノート

反応式

HRID 1696731 の反応式
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7].[Mg].[CH3:9][O:10][CH2:11][CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O>C(OCC)C>[CH3:9][O:10][CH2:11][CH2:12][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7]

参加物

5

反応物 3

HCID 843142-Bromo-3-methylthiopheneHCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)HCID 5462224Magnesium

生成物 1

HCID 668571532-(2-Methoxy-ethyl)-3-methyl-thiophene

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A part of a solution containing 2-bromo-3-methylthiophene CAS 14282-76-9 (1.5 g, 8.5 mmol) in dry diethyl ether was added drop-wise to a suspension of magnesium (308 mg, 12.7 mmol, 1.5 equiv.) in dry diethyl ether,until the mixture started to reflux. The remaining solution was added dropwise. A solution of toluene-4-sulfonic acid 2-methoxy-ethyl ester (2.9 g, 12.7 mmol, 1.5 equiv.) in dry diethyl ether was added dropwise at room temp., then the mixture was refluxed for two hours. After cooling down to room temp., the mixture was quenched with ammonium chloride solution saturated and extracted with tert. butylmethyl ether. The combined organic extracts were washed with water and brine, dried over magnesiumsulfate-dihydrate and purified on silica gel with eluent n-heptane and tert.butylmethyl ether. The title compound was obtained as light yellow oil: 490 mg, GC-MS (EI) M=156.

後処理

  1. additionwas added drop-wise
  2. temperatureto reflux
  3. additionThe remaining solution was added dropwise
  4. temperaturethe mixture was refluxed for two hours
  5. temperatureAfter cooling down to room temp.
  6. customthe mixture was quenched with ammonium chloride solution saturated
  7. extractionextracted with tert. butylmethyl ether
  8. washThe combined organic extracts were washed with water and brine
  9. dry with materialdried over magnesiumsulfate-dihydrate
  10. custompurified on silica gel with eluent n-heptane and tert.butylmethyl ether

出典と根拠

ORDレコード
ord-f836c39c55474ca4ad93cb9e0fc54551
出典データセット
uspto-grants-2012_04
特許番号
US08163778B2

反応ノート

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