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Morpholine → 5-Hydroxy-2-(morpholinomethyl)-4H-pyran-4-one

HRID 2108873
ノート
印刷プレビュー

反応式

HRID 2108873 の反応式
Br[CH2:2][C:3]1[O:4][CH:5]=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C(#N)C>[OH:10][C:6]1[C:7](=[O:9])[CH:8]=[C:3]([CH2:2][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[O:4][CH:5]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 8083MorpholineHCID 10976603KOJIC ACID, 2-BROMOMETHYL ANALOG

生成物 1

HCID 33182525-Hydroxy-2-(morpholinomethyl)-4H-pyran-4-one収率 93.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

2-(Bromomethyl)-5-hydroxy-4H-pyran-4-one 21 (5.0 g, 24.4 mmol), morpholine (4.3 mL, 48.8 mmol) and acetonitrile (120 mL) were charged in a 250 ml round-bottomed flask equipped with a magnetic stirrer. The reaction mixture was stirred for 3 h at 80° C. Acetonitrile was evaporated and the residu was extracted with EtOAc (400 mL). The organic layer was washed with water (20 mL), brine (2×20 mL), dried over MgSO4, filtered and evaporated to dryness. Diethyl ether (25 mL) was added and the product was precipitated and filtered to give after drying 5-hydroxy-2-(morpholinomethyl)-4H-pyran-4-one 22 (4.8 g, 72% yield) as a white solid.

後処理

  1. customequipped with a magnetic stirrer
  2. customAcetonitrile was evaporated
  3. extractionthe residu was extracted with EtOAc (400 mL)
  4. washThe organic layer was washed with water (20 mL), brine (2×20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. additionDiethyl ether (25 mL) was added
  9. customthe product was precipitated
  10. filtrationfiltered
  11. customto give

出典と根拠

ORDレコード
ord-756e52f0aa7c4aa68f50ec2817f6305d
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07514432B2

反応ノート

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