Ethylene Glycol → 2-Bromo-6-(1,3-dioxolan-2-yl)pyridine

HRID 931086ノート

反応式

HRID 931086 の反応式
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[N:7]=1

参加物

6

反応物 2

HCID 174Ethylene GlycolHCID 27570096-Bromopyridine-2-carbaldehyde

生成物 1

HCID 1186132-Bromo-6-(1,3-dioxolan-2-yl)pyridine収率 99.2%

試薬・触媒・溶媒 3

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-bromopyridine-2-carbaldehyde (3 g, 16.22 mmol) in toluene (60 mL) was added ethylene glycol (4.97 g, 80.2 mmol) and p-toluenesulphonic acid (0.152 g, 0.8 mmol). The reaction mixture was refluxed for 3 h. The solvent was removed under reduced pressure to afford the crude which was dissolved in ethyl acetate and washed with water. The organic layers were washed with a brine solution, and dried over sodium sulfate. The solvent was removed under reduced pressure to afford 2-bromo-6-(1,3-dioxolan-2-yl)pyridine (3.7 g). The material was used for the next step without further purification.

後処理

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customThe solvent was removed under reduced pressure
  3. customto afford the crude which
  4. washwashed with water
  5. washThe organic layers were washed with a brine solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-45a1a7a62fd74303b1573ae4219afdec
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

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