1-(Chloromethoxy)-2-methoxyethane → 2-Bromo-3-[2-(methoxyethoxymethoxy)ethyl]thiophene

HRID 1651644ノート

反応式

HRID 1651644 の反応式
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][OH:9].[CH3:10][O:11][CH2:12][CH2:13][O:14][CH2:15]Cl.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][O:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15]

参加物

5

反応物 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 193595722-(2-Bromothiophen-3-yl)ethan-1-ol

生成物 1

HCID 540438672-Bromo-3-[2-(methoxyethoxymethoxy)ethyl]thiophene収率 91.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-bromo-3-(2-hydroxyethyl)thiophene (40.0 g, 0.193 mol) in methylene chloride (200 ml) was cooled in ice and methoxyethoxymethyl chloride (41.9 g, 0.336 mol) was added with stirring. After several minutes N,N-diisopropylethylamine (44.3 g, 0.336 mol) was added and the solution was stirred overnight at room temperature. The solvent was removed in vacuo and the residue was taken up in ether (150 ml) and water (75 ml). The ether layer was separated and was washed with saturated NaHCO3 solution and with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo at room temperature to give 52.1 g of an amber liquid. TLC indicated that the product was pure and NMR confirmed the structure. Field desorption mass spectral analysis gave a molecular ion of M/Z 294. The yield was 91%.

後処理

  1. stirringthe solution was stirred overnight at room temperature
  2. customThe solvent was removed in vacuo
  3. customThe ether layer was separated
  4. washwas washed with saturated NaHCO3 solution and with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo at room temperature

出典と根拠

ORDレコード
ord-44d6c280ec6644ab9124722c76a35269
出典データセット
uspto-grants-1990_05
特許番号
US04929637

反応ノート

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