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

HRID 1830557

反応式

HRID 1830557 の反応式
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]=[O:8].[CH2:9](O)[CH2:10][OH:11].C([O-])(O)=O.[Na+]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]1[O:11][CH2:10][CH2:9][O:8]1

参加物

6

反応物 3

HCID 174Ethylene Glycol2 回HCID 516892Sodium BicarbonateHCID 33672713-Bromo-2-furaldehyde

生成物 1

HCID 123723092-(3-Bromofuran-2-yl)-1,3-dioxolane収率 92.4%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 241Benzene溶媒2 回

実験手順

3-Bromo-2-furaldehyde (14.22 g, 81.3 mmol) is combined with ethylene glycol (6.55 mL, 117.4 mmol) and para-toluene sulfonic acid monohydrate (772 mg, 4.06 mmol) in benzene (200 mL) and heated to reflux with a Dean-Stark trap for 5 h. Additional ethylene glycol (1.64 mL, 29.41 mmol) and benzene (150 mL) are added and the solution is heated for an additional 2 h. The mixture is cooled to rt, treated with saturated NaHCO3 and stirred for 0.5 h. The layers are separated and the organics are dried over Na2SO4 and concentrated to a brown oil (18.8 g). The crude material is chromatographed over 700 g slurry-packed silica gel, eluting with 15% EtOAc/hexane. The appropriate fractions are combined and concentrated in vacuo to afford 16.45 g (92%) of 2-(3-bromo-2-furyl)-1,3-dioxolane as a yellow-orange oil. MS (EI) m/z: 218 (M+).

後処理

  1. temperatureheated
  2. temperatureto reflux with a Dean-Stark trap for 5 h
  3. temperaturethe solution is heated for an additional 2 h
  4. customThe layers are separated
  5. dry with materialthe organics are dried over Na2SO4
  6. concentrationconcentrated to a brown oil (18.8 g)
  7. customThe crude material is chromatographed over 700 g slurry-packed silica gel
  8. washeluting with 15% EtOAc/hexane
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a7b671f4135347199eed9f465f27011d
出典データセット
uspto-grants-2006_06
特許番号
US07067515B2

関連ノート

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