碳酸钾 → 5-苯基-2-糠醛

HRID 896474

反应方程式

HRID 896474 反应方程式
Br[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:9]1([C:2]2[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参与物

7

反应物 3

HCID 11430碳酸钾HCID 66827苯硼酸HCID 6003285-溴-2-呋喃甲醛

产物 1

HCID 27694205-苯基-2-糠醛

试剂、催化剂与溶剂 3

HCID 74236四丁基溴化铵催化剂HCID 167845palladium acetate催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次

实验过程

A solution of 5-bromo-furan-2-carbaldehyde (1.08 g, 6.16 mmol, 1 eq), phenylboronic acid (0.90 g, 7.39 mmol, 1.1 eq), tetrabutylammonium bromide (1.99 g, 6.16 mmol, 1 eq), palladium acetate (30 mg, 0.0.12 mmol 0.02 eq), K2CO3 (2.13 g, 15.4 mmol, 2.5 eq) in water (10 mL) is stirred under nitrogen at rt overnight. The reaction is diluted with 40 mL water and extracted with EtOAc (3×100 mL). The organic layers are combined and stirred with charcoal for 30 min, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure to give 5-phenyl-furan-2-carbaldehyde as an oil. The product is purified by silica gel chromatography using a Biotage Flash 40M column (10% EtOAc/heptane).

后处理

  1. extractionextracted with EtOAc (3×100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe solvent is removed under reduced pressure

来源与证据

ORD记录
ord-98b5835f61b24615b76ebd54d47bdad3
来源数据集
uspto-grants-2005_07
专利号
US06919359B2

关联笔记

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