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

HRID 458413ノート

反応式

HRID 458413 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b38d458893a746409b3db3f851fa7406
出典データセット
uspto-grants-2007_03
特許番号
US07189851B2

反応ノート

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