6-Bromopyridine-2-carbaldehyde → 1-(6-Bromo-2-pyridinyl)ethanol

HRID 460198ノート

反応式

HRID 460198 の反応式
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][Mg]I>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:9])[CH3:10])[CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 178418373HCID 178418373、化合物

生成物 1

HCID 110634791-(6-Bromo-2-pyridinyl)ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

6-Bromo-2-pyridine carboxaldehyde (1.0 g, 5.37 mmol) in dry THF (20 mL) was cooled to −78° C. followed by adding MeMgI (2.0 mL, 5.91 mmol) dropwise via the addition funnel. The cooling bath was removed. The resulting mixture was stirred for 1 h then quenched with sat. NH4Cl. Solvent was removed. The residue was partitioned between water and CHCl3. The organic layer was washed with H2O, brine, dried over MgSO4. Solvent was removed and crude compound was purified by chromatography on silica gel. Elution with hexane:acetone mixture (70:30) gave a white solid. MS m/z: 201.9(M+H). Calc'd. for C7H8BrNO-200.98.

後処理

  1. customThe cooling bath was removed
  2. customthen quenched with sat. NH4Cl
  3. customSolvent was removed
  4. customThe residue was partitioned between water and CHCl3
  5. washThe organic layer was washed with H2O, brine
  6. dry with materialdried over MgSO4
  7. customSolvent was removed
  8. customcrude compound was purified by chromatography on silica gel
  9. washElution with hexane
  10. customacetone mixture (70:30) gave a white solid

出典と根拠

ORDレコード
ord-a10fa372cfd54433be8a370844bcf3dd
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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