Imidazole → 2-[(2-Chloro-5-methylpyridin-3-yl)(hydroxy)methyl]cyclopent-2-en-1-one

HRID 1445552ノート

反応式

HRID 1445552 の反応式
[Cl:1][C:2]1[N:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5].N1C=CN=C1.[C:16]1(=[O:21])[CH2:20][CH2:19][CH:18]=[CH:17]1>CO.O>[Cl:1][C:2]1[C:3]([CH:4]([OH:5])[C:17]2[C:16](=[O:21])[CH2:20][CH2:19][CH:18]=2)=[CH:6][C:7]([CH3:10])=[CH:8][N:9]=1

参加物

6

反応物 3

HCID 795ImidazoleHCID 135882-Cyclopenten-1-oneHCID 98340182-Chloro-5-methylpyridine-3-carbaldehyde

生成物 1

HCID 588802332-[(2-Chloro-5-methylpyridin-3-yl)(hydroxy)methyl]cyclopent-2-en-1-one収率 98%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

実験手順

The clear solution of 2-Chloro-5-methylnicotinaldehyde (10 mmol, 1.55 g) and imidazole (10 mmol, 0.68 g) in 50 ml. of MeOH was slowly charged with 50 ml. of deionized water. To a stirred homogeneous reaction mixture was added 2-cyclopenten-1-one (10.2 mmol., 0.88 g) at room temperature and reaction progress was monitored by TLC. Upon completion of the reaction, excess MeOH was removed under reduced pressure, washed with water and extracted with CHCl3 thrice. Combined organic layers were washed with brine solution twice. The organic layer was concentrated and column chromatography of the crude product on silica gel, using 30% EtOAC in hexane as eluent, gave pure Baylis-Hillman adduct in 98% yield (2.32 g)

後処理

  1. customreaction progress
  2. customwas removed under reduced pressure
  3. washwashed with water
  4. extractionextracted with CHCl3 thrice
  5. washCombined organic layers were washed with brine solution twice
  6. concentrationThe organic layer was concentrated
  7. customgave pure Baylis-Hillman adduct in 98% yield (2.32 g)

出典と根拠

ORDレコード
ord-7af05eefcb9c4456a48ca34ef28d7ae3
出典データセット
uspto-grants-2010_02
特許番号
US07666883B2

反応ノート

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