乙醚 → 5-苯基-2-噻吩甲醛

HRID 412004

反应方程式

HRID 412004 反应方程式
Br[C:2]1[S: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.[Na+].[Na+].CCOCC>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:9]1([C:2]2[S: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 4

HCID 3283乙醚HCID 10340Carbonic acid sodium salt (1:2)HCID 66827苯硼酸HCID 784285-溴噻吩-2-甲醛

产物 1

HCID 1770535-苯基-2-噻吩甲醛收率 91.9%

试剂、催化剂与溶剂 2

HCID 178418397HCID 178418397，化合物催化剂HCID 8028四氢呋喃溶剂2 次

实验过程

5-Bromothiophene-2-carboxaldehyde (1.0 g, 5.2 mmol) is added to a solution of tetrakis(triphenylphosphine)palladium(0) (180 mg, 0.16 mol) in degassed THF (10 mL). The resulting solution is stirred for 5 minutes and then a solution of phenylboronic acid (760 mg, 6.2 mmol) in THF (10 mL) is added followed by aqueous Na2CO3 (2M, 5.2 mL). The mixture is heated at reflux for 24 h. The reaction mixture is allowed to cool, poured into ether, and washed twice with water. The ether layer is dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (1:1 hexanes/CH2Cl2) to yield 900 mg (91%) of 5-phenylthiophene-2-carboxaldehyde. 1H NMR (300MHz, CDCl3)δ7.38-7.45, 7.65-7.68, 7.73, 9.88.

后处理

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 h
  3. temperatureto cool
  4. washwashed twice with water
  5. dry with materialThe ether layer is dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash column chromatography (1:1 hexanes/CH2Cl2)

来源与证据

ORD记录
ord-9042e8cf7efe4b88ac999d58addddc10
来源数据集
uspto-grants-2003_05
专利号
US06562816B2

关联笔记

加载中…