苯磺酰氯 → 2-Pyrrolidinone, 5-(phenylmethoxy)-1-(phenylsulfonyl)-

HRID 1761886笔记

反应方程式

HRID 1761886 反应方程式
[CH2:1]([O:8][CH:9]1[NH:13][C:12](=[O:14])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(OCC)C>[C:25]1([S:31]([N:13]2[CH:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:10][CH2:11][C:12]2=[O:14])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参与物

5

反应物 3

HCID 7369苯磺酰氯HCID 2724254双(三甲基硅基)氨基钠HCID 15078419HCID 15078419，化合物

产物 1

HCID 30867282-Pyrrolidinone, 5-(phenylmethoxy)-1-(phenylsulfonyl)-收率 29.5%

试剂、催化剂与溶剂 1

HCID 3283乙醚溶剂2 次

反应条件

温度
0 °C

实验过程

At ambient temperature and under an inert atmosphere, 4.40 g of 5-benzyloxypyrrolidin-2-one is added to a solution of 4.64 g of sodium bis(trimethylsilyl) amide in 350 cm3 of anhydrous ethyl ether. The mixture is agitated for 30 minutes, then cooled to 0° C., and a solution of 4.06 g of benzenesulphonyl chloride in 30 cm3 of anhydrous ether is added, while maintaining the temperature at 0° C. The temperature is allowed to return to the ambient, then, after filtering and evaporating the solvent under reduced pressure, the residue is chromatographed on silica, eluting with a mixture of ethyl acetate and n-hexane (1-2). After re-crystallizing from a mixture of benzene and n-hexane (1-3), 2.25 g of the expected product is obtained, m.p. 80°-81° C.

后处理

  1. temperaturewhile maintaining the temperature at 0° C
  2. filtrationafter filtering
  3. customevaporating the solvent under reduced pressure
  4. customthe residue is chromatographed on silica
  5. washeluting with a mixture of ethyl acetate and n-hexane (1-2)
  6. customAfter re-crystallizing from a mixture of benzene and n-hexane (1-3)

来源与证据

ORD记录
ord-762daad8e7854ce6a5774a985f567c66
来源数据集
uspto-grants-1989_05
专利号
US04829079

反应笔记

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