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

HRID 1651644노트

반응식

HRID 1651644 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-44d6c280ec6644ab9124722c76a35269
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04929637

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