2,6-Dibromopyridine → 2-Bromo-6-[(oxolan-3-yl)oxy]pyridine

HRID 460219ノート

反応式

HRID 460219 の反応式
[OH:1][C@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[N:11]=1>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:1][CH:2]2[CH2:6][CH2:5][O:4][CH2:3]2)[N:11]=1

参加物

5

反応物 3

HCID 122742,6-DibromopyridineHCID 24758Sodium hydrideHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

生成物 1

HCID 187717992-Bromo-6-[(oxolan-3-yl)oxy]pyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (S)-(+)-3-hydroxy-tetrahydrofuran (0.34 mL, 4.2 mmol) and dry THF (20 mL) was added NaH (0.17 g, 4.2 mmol, 60%) under N2 at RT. After 5 min, added 2,6-dibromopyridine. Stirred at RT for 4 h. Quenched with H2O and extracted with EtOAc. Washed organic layer with saturated NH4Cl, brine, dried (MgSO4) and concentrated in vacuo to give 2-bromo-6-(tetrahydro-furan-3-yloxy)-pyridine as a clear, colorless oil. MS m/z: 245.2 (M+H). Calc'd for C9H10BrNO2-244.09.

後処理

  1. customQuenched with H2O
  2. extractionextracted with EtOAc
  3. dry with materialWashed organic layer with saturated NH4Cl, brine, dried (MgSO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-db13b12650454b8280035d35ac0dbbb4
出典データセット
uspto-grants-2007_03
特許番号
US07196104B2

反応ノート

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