Ethylene Glycol → 2-(4-Bromothiophen-2-yl)-1,3-dioxolane

HRID 458413노트

반응식

HRID 458413 반응식
C1C=CC=CC=1.[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[O:14])[S:11][CH:12]=1.[CH2:15](O)[CH2:16][OH:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC.O>[Br:7][C:8]1[CH:9]=[C:10]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)[S:11][CH:12]=1

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 877924-Bromothiophene-2-carbaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 38572552-(4-Bromothiophen-2-yl)-1,3-dioxolane수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

A benzene (55 mL) solution of 4-bromo-2-thiophene carboxaldehyde (9.76 g 51.09 mmol), ethylene glycol (8.55 mL, 153.26 mmol) and p-toluenesulfonic acid monohydrate (0.972 g, 5.11 mmol) was refluxed with azeotropic removal of H2O for 6 h and then cooled to ambient temperature. The reaction mixture was diluted with Et2O and the organics washed with sat'd NaHCO3, brine and then dried (MgSO4), filtered and concentrated. Chromatography on silica gel using 95:5 Hexanes:EtOAc eluted the product to provide the title compound upon concentration as a yellow oil (10.76 g 90% yield): 1H NMR (CDCl3, 400 MHz) δ 7.22 (s, 1H), 7.08 (s, 1H), 6.07 (s, 1H), 4.14–4.00 (m, 4H).

후처리

  1. washthe organics washed with sat'd NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washChromatography on silica gel using 95:5 Hexanes:EtOAc eluted the product

출처 및 근거

ORD 기록
ord-b38d458893a746409b3db3f851fa7406
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189851B2

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