丙二酸二甲酯 → dimethyl (S)-alpha-(1,3-diphenyl-2-propen-1-yl)malonate

HRID 658287笔记

反应方程式

HRID 658287 反应方程式
C(O[CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)C.[C:20]([O:27][CH3:28])(=[O:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.C([O-])(=O)C.[K+].[Cl-].[NH4+]>ClCCl.C(OCC)C>[C:14]1([C@H:5]([CH:21]([C:20]([O:27][CH3:28])=[O:26])[C:22]([O:24][CH3:25])=[O:23])[CH:6]=[CH:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参与物

8

反应物 5

HCID 7943丙二酸二甲酯HCID 25517氯化铵HCID 517044乙酸钾HCID 6058773-Acetoxy-1,3-diphenylpropeneHCID 6913588N,O-双三甲硅基乙酰胺

产物 1

HCID 45115416dimethyl (S)-alpha-(1,3-diphenyl-2-propen-1-yl)malonate

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂HCID 6344二氯甲烷溶剂2 次

实验过程

In 0.5 ml of dichloromethane were suspended 0.9 mg (2.5 μmol) of [PdCl(η3-C3H5)]2 and 1.8 mg (5.5 μmol) of (R,R)-t-Bu-QuinoxP* (1), followed by stirring at room temperature for 10 to 30 minutes. To the resulting solution were added a solution of 126 mg (0.50 mmol) of 1,3-diphenyl-2-propenyl acetate in 1.5 ml of dichloromethane, 171 μl (1.50 mmol) of dimethyl malonate, 367 μl (1.50 mmol) of N,O-bis(trimethylsilyl)acetamide (BSA), and a trace amount of potassium acetate. The reaction system was stirred at room temperature for 1 hour. The reaction mixture was diluted with diethyl ether, and a saturated aqueous solution of ammonium chloride was added to stop the reaction. The resulting mixture was extracted with diethyl ether, and the organic layer was washed with a sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate. Any volatile matter was evaporated off, and the residue was purified by silica gel column chromatography.

后处理

  1. stirringThe reaction system was stirred at room temperature for 1 hour
  2. customthe reaction
  3. extractionThe resulting mixture was extracted with diethyl ether
  4. washthe organic layer was washed with a sodium chloride aqueous solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customAny volatile matter was evaporated off
  7. customthe residue was purified by silica gel column chromatography

来源与证据

ORD记录
ord-0b47e6b8dd0c4e6cba6470c6760811ac
来源数据集
uspto-grants-2011_12
专利号
US08076480B2

反应笔记

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