Morpholine → [2-(Morpholin-4-yl)phenyl]methanol

HRID 1678578

反応式

HRID 1678578 の反応式
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+]>CN(C=O)C.CO.O>[N:10]1([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

参加物

8

反応物 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 2776562[2-(Morpholin-4-yl)phenyl]methanol収率 30%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

2-Fluorobenzaldehyde (1.0 g, 8.1 mmol) was dissolved in DMF (20 mL), morpholine (2.0 mL) and potassium carbonate (1.1 g, 8.1 mmol) were added thereto, and then the mixture was stirred at 80° C. for 2 days. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=98:2 to 60:40) to give an oily matter. The resulting oily matter was dissolved in methanol (20 mL), sodium borohydride (613 mg, 16.2 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure to give the title compound (474 mg, yield 30%).

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=98:2 to 60:40)
  5. customto give an oily matter
  6. stirringthe mixture was stirred at room temperature for 3 hours
  7. extractionthe reaction mixture was extracted with ethyl acetate
  8. customThe extract was dried
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7a1371fc483e4f009993f81201af17eb
出典データセット
uspto-grants-2011_08
特許番号
US08008525B2

関連ノート

読み込み中…