海萝胶 → HCID 178418663，化合物

HRID 5259

反应方程式

HRID 5259 反应方程式
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]=[CH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](O)=[O:44])=[CH:30][CH:29]=1.Cl>CN(C)C=O.CN(C)C1C=CN=CC=1>[OH:3][C:2]1[CH2:4][O:5][C:6](=[O:7])[C:1]=1[C:43](=[O:44])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=[CH:34][C:31]1[CH:30]=[CH:29][C:28]([Cl:27])=[CH:33][CH:32]=1

参与物

8

反应物 5

HCID 313海萝胶HCID 8471三乙胺HCID 5212614-羟乙酰乙酸内酯HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐HCID 5440741310-(4-Chlorophenyl)dec-9-enoic acid

产物 1

HCID 178418663HCID 178418663，化合物收率 58.3%

试剂、催化剂与溶剂 2

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

To a stirring solution of 189 mg (1.89 mmol) of tetronic acid in 15 mL of dimethylformamide is added 290 μL (2.08 mmol) of triethylamine and 8 mg (66 μmol) of 4-dimethylaminopyridine at 0° C. Next, 427 mg (2.22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 690 mg (2.20 mmol) of 10-(4-chlorophenyl)dec-9-enoic acid as a mixture of E and Z isomers are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ethyl acetate. The combined organic layers are washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue is purified via flash chromatography on a 40 mm×150 mm silica gel column eluting with 5% methanol/ethyl acetate to give 400 mg (58%) of pure 4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodec-9-enyl] -2(5H)-furanone as a mixture of E and Z isomers.

后处理

  1. additionare added
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified via flash chromatography on a 40 mm×150 mm silica gel column
  7. washeluting with 5% methanol/ethyl acetate

来源与证据

ORD记录
ord-bdf94d64f6764381bbbb7b18839e7b85
来源数据集
uspto-grants-1993_09
专利号
US05242945

关联笔记

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