2-Bromopyridine → (+/-)-N-[4-[hydroxy(2-pyridinyl)methyl]phenyl]-acetamide

HRID 429860

反応式

HRID 429860 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[CH:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=1)=[O:14]>CCCCCC.C1COCC1>[OH:14][CH:13]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:19][CH:20]=1

参加物

6

反応物 3

HCID 79732-BromopyridineHCID 739424-AcetamidobenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 10131015(+/-)-N-[4-[hydroxy(2-pyridinyl)methyl]phenyl]-acetamide収率 17.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

Butyllithium, 1.6M in hexane (146 ml) was added dropwise at −78° C. under N2 flow to a solution of 2-bromopyridine (0.1348 mol) in THF (300 ml). The mixture was stirred at −78° C. for 20 minutes. A solution of N-(4-formylphenyl) acetamide (0.1226 mol) in THF (300 ml) was added at −60° C./−70° C. The mixture was stirred at −60° C./−70° C. for 1 hour, then poured out into ice water and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue (27 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.1). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from diethyl ether and 2-propanone. The precipitate was filtered off and dried, yielding 5.09 g (17%) (±)-N-[4-[hydroxy(2-pyridinyl)methyl]phenyl]-acetamide (compound 688).

後処理

  1. stirringThe mixture was stirred at −60° C./−70° C. for 1 hour
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (27 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.1)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue was crystallized from diethyl ether and 2-propanone
  11. filtrationThe precipitate was filtered off
  12. customdried

出典と根拠

ORDレコード
ord-b7f0d49675dd4fb9b4ea2df117cfda2b
出典データセット
uspto-grants-2001_11
特許番号
US06319939B1

関連ノート

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