2-Bromo-6-(1,3-dioxolan-2-yl)pyridine → HCID 89853573、化合物

HRID 931087ノート

反応式

HRID 931087 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[N:3]=1.C([Li])CCC.[O:18]1[CH2:21][C:20](=[O:22])[CH2:19]1>O1CCCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:4]1[N:3]=[C:2]([C:20]2([OH:22])[CH2:21][O:18][CH2:19]2)[CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 1186132-Bromo-6-(1,3-dioxolan-2-yl)pyridineHCID 150242543-OxetanoneHCID 178418339Butyllithium

生成物 1

HCID 89853573HCID 89853573、化合物収率 27%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2-bromo-6-(1,3-dioxolan-2-yl)pyridine (2.49 g, 10.8 mmol) in anhydrous tetrahydrofuran (40 mL) was added a solution of n-butyllithium (2.5 M, 4.3 mL, 10.8 mmol) at −78° C. After stirring for 30 min., a solution of oxetan-3-one (0.6 g, 8.32 mmol) in anhydrous tetrahydrofuran (12 mL) was added slowly and the mixture was stirred at that temperature for 1 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the crude compound. The crude material was purified via preparative TLC eluting with 35% ethyl acetate in petroleum ether to afford 3-(6-(1,3-dioxolan-2-yl)pyridin-2-yl)oxetan-3-ol (500 mg, 27%). MS (ES+) (M+H) 224.20; LCMS retention time: 2.76 minutes (Method S).

後処理

  1. stirringthe mixture was stirred at that temperature for 1 h
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude compound
  9. customThe crude material was purified via preparative TLC
  10. washeluting with 35% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-8e1ba8432d604ab0a3ab620def49ed29
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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